TW202311495A - Nitrogen-containing heterocyclic compounds for organic electroluminescent devices - Google Patents

Nitrogen-containing heterocyclic compounds for organic electroluminescent devices Download PDF

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TW202311495A
TW202311495A TW111116223A TW111116223A TW202311495A TW 202311495 A TW202311495 A TW 202311495A TW 111116223 A TW111116223 A TW 111116223A TW 111116223 A TW111116223 A TW 111116223A TW 202311495 A TW202311495 A TW 202311495A
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菲利普 史托希爾
安瑪 帕姆
盧分 凌吉
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德商麥克專利有限公司
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Abstract

The present invention relates to nitrogen-containing heterocyclic compounds suitable for use in electronic devices, and to electronic devices, especially organic electroluminescent devices, comprising these compounds.

Description

用於有機電致發光裝置之含氮雜環化合物Nitrogen-containing heterocyclic compounds for organic electroluminescent devices

本發明關於用於電子裝置，尤其用於有機電致發光裝置之含氮雜環化合物，及包含該等雜環化合物之電子裝置，尤其為有機電致發光裝置。The present invention relates to nitrogen-containing heterocyclic compounds used in electronic devices, especially organic electroluminescent devices, and electronic devices comprising the heterocyclic compounds, especially organic electroluminescent devices.

在有機電致發光裝置中所使用之發光材料時常為磷光有機金屬錯合物或螢光化合物。通常對電致發光裝置的改進仍有需要。 US 6,322,908和WO 03/001569 A2 揭示可用於有機電致發光裝置中的多環化合物。沒有揭示根據本發明之化合物。另外，出版物J. Org. Chem. 1995, 60, 2344-2352說明化合物(包括含氮雜環化合物)的光化學性質。含氮雜環化合物之合成詳述於Chin. J. Chem. 2011, 29, 2769中。然而，在引用之出版物中沒有說明該等化合物在有機電致發光裝置中的用途。 一般而言，對該等含氮雜環化合物的改進仍有需要，例如用作為發光體，尤其用作為螢光發光體，特別關於壽命及色純度，但亦關於裝置的效率及操作電壓。 因此，本發明之目的係提供適合用於有機電子裝置，尤其用於有機電致發光裝置且在用於此裝置時得到良好的裝置性質之化合物，且提供對應的電子裝置。 由本發明所解決的問題更特別地在於提供導致高壽命、良好效率及低操作電壓之化合物。 另外，化合物應具有極佳的可加工性，且化合物尤其應顯示良好的溶解性。 可考慮由本發明所解決的其他問題在於提供適合用於磷光或螢光電致發光裝置，尤其用作為發光體之化合物。由本發明所解決的問題更特別地在於提供適合於紅色、綠色和藍色電致發光裝置之發光體。 另外，化合物，尤其當其用作為有機電致發光裝置之發光體時，應得到具有極佳的色純度之裝置。 可考慮由本發明所解決的其他問題在於提供適合用於磷光或螢光電致發光裝置，尤其用作為基質材料之化合物。由本發明所解決的問題更特別地在於提供適合於發紅色、發黃色和發藍色磷光之電致發光裝置之基質材料。 另外，化合物，尤其當其用作為有機電致發光裝置之基質材料或電子傳輸材料時，應得到具有極佳的色純度之裝置。 可考慮的其他問題在於提供非常便宜且品質恆定的具有極佳性能之電子裝置。 此外，應有可能使電子裝置使用或適應於許多目的。電子裝置的性能更特別地應在寬廣的溫度範圍內得以維持。 已驚人地發現此目的係由下文詳述之特定化合物達成，該化合物具有用於電致發光裝置之非常良好的適合性且得到顯示非常良好的性質之有機電致發光裝置，尤其關於壽命、色純度、效率及操作電壓。本發明因此提供該等化合物及包含該等化合物之電子裝置，尤其為有機電致發光裝置。 The light-emitting materials used in organic electroluminescent devices are often phosphorescent organometallic complexes or fluorescent compounds. There is still a need for improvements in electroluminescent devices in general. US 6,322,908 and WO 03/001569 A2 disclose polycyclic compounds useful in organic electroluminescent devices. No compounds according to the invention are disclosed. In addition, the publication J. Org. Chem. 1995, 60, 2344-2352 describes the photochemical properties of compounds, including nitrogen-containing heterocycles. The synthesis of nitrogen-containing heterocyclic compounds is detailed in Chin. J. Chem. 2011, 29, 2769. However, the use of these compounds in organic electroluminescent devices is not described in the cited publications. In general, there is still a need for improvement of such nitrogen-containing heterocyclic compounds, for example for use as emitters, especially as fluorescent emitters, especially with regard to lifetime and color purity, but also with regard to efficiency and operating voltage of devices. It was therefore an object of the present invention to provide compounds which are suitable for use in organic electronic devices, in particular organic electroluminescent devices, and which give good device properties when used in such devices, and to provide corresponding electronic devices. The problem solved by the present invention is more particularly to provide compounds leading to high lifetime, good efficiency and low operating voltage. In addition, the compounds should have excellent processability, and the compounds should especially exhibit good solubility. A further problem which may be considered to be solved by the present invention consists in providing compounds which are suitable for use in phosphorescent or fluorescent electroluminescent devices, in particular as emitters. The problem solved by the present invention is more particularly to provide an emitter suitable for red, green and blue electroluminescent devices. Furthermore, the compounds, especially when used as emitters for organic electroluminescent devices, should result in devices with excellent color purity. A further problem which may be considered to be solved by the present invention consists in providing compounds which are suitable for use in phosphorescent or fluorescent electroluminescent devices, in particular as matrix materials. The problem solved by the invention consists more particularly in providing matrix materials suitable for red-, yellow- and blue-phosphorescent electroluminescent devices. In addition, the compounds, especially when they are used as matrix materials or electron-transport materials for organic electroluminescent devices, should result in devices with excellent color purity. Another problem that can be considered is that of providing electronic devices with excellent performance at very low cost and with constant quality. Furthermore, it should be possible to use or adapt electronic devices for many purposes. The performance of electronic devices should more particularly be maintained over a broad temperature range. It has surprisingly been found that this object is achieved by specific compounds detailed below which have a very good suitability for use in electroluminescent devices and give organic electroluminescent devices which exhibit very good properties, especially with regard to lifetime, color Purity, efficiency and operating voltage. The present invention therefore provides these compounds and electronic devices comprising these compounds, in particular organic electroluminescent devices.

本發明提供包含至少一種式(I)之結構之化合物，較佳為式(I)化合物，

Figure 02_image003
其中環Ar a在各情況下為相同的或不同的且為具有5至60個芳族環原子且可經一或多個Ar或R a基團取代之芳族或雜芳族環系統，環Ar b在各情況下為相同的或不同的且為具有5至60個芳族環原子且可經一或多個Ar或R b基團取代之芳族或雜芳族環系統； 且其中所使用之其他符號及標號係如下： W a、W b在各情況下為相同的或不同的且為O或S，較佳為O； Ar    在各情況下為相同的或不同的且為具有5至60個芳族環原子且可經一或多個R基團取代之芳族或雜芳族環系統；Ar基團可與至少一個Ar、R、R a、R b基團或另一基團形成環系統； R、R a、R b在各情況下為相同的或不同的且為H、D、OH、F、Cl、Br、I、CN、NO 2、N(Ar') 2、N(R 1) 2、C(=O)N(Ar') 2、C(=O)N(R 1) 2、C(Ar') 3、C(R 1) 3、Si(Ar') 3、Si(R 1) 3、B(Ar') 2、B(R 1) 2、C(=O)Ar'、C(=O)R 1、P(=O)(Ar') 2、P(=O)(R 1) 2、P(Ar') 2、P(R 1) 2、S(=O)Ar'、S(=O)R 1、S(=O) 2Ar'、S(=O) 2R 1、OSO 2Ar'、OSO 2R 1、具有1至40個碳原子的直鏈烷基、烷氧基或硫烷氧基或具有2至40個碳原子的烯基或炔基、或具有3至20個碳原子的支鏈或環狀烷基、烷氧基或硫烷氧基，其中該等烷基、烷氧基、硫烷氧基、烯基或炔基可在各例子中經一或多個R 1基團取代，其中一或多個不相鄰的CH 2基團可經R 1C=CR 1、C≡C、Si(R 1) 2、C=O、C=S、C=Se、C=NR 1、-C(=O)O-、-C(=O)NR 1-、NR 1、P(=O)(R 1)、-O-、-S-、SO或SO 2置換、或具有5至60個芳族環原子且可在各例子中經一或多個R 1基團取代之芳族或雜芳族環系統、或具有5至60個芳族環原子且可經一或多個R 1基團取代之芳氧基或雜芳氧基、或具有5至60個芳族環原子且可經一或多個R 1基團取代之雜芳硫基、或具有5至60個芳族環原子且可經一或多個R 1基團取代之二芳胺基、芳基雜芳胺基、二雜芳胺基、或具有5至60個芳族環原子且在烷基中的1至10個碳原子可經一或多個R 1基團取代之芳烷基或雜芳基烷基；同時，兩個R、R a、R b基團亦可一起或與另一基團形成環系統； Ar'   在各情況下為相同的或不同的且為具有5至60個芳族環原子且可經一或多個R 1基團取代之芳族或雜芳族環系統；同時，與相同的碳原子、矽原子、氮原子、磷原子或硼原子鍵結之兩個Ar’基團亦有可能經由單鍵之橋或選自下列之橋接合在一起：B(R 1)、C(R 1) 2、Si(R 1) 2、C=O、C=NR 1、C=C(R 1) 2、O、S、S=O、SO 2、N(R 1)、P(R 1)和P(=O)R 1； R 1在各情況下為相同的或不同的且為H、D、F、Cl、Br、I、CN、NO 2、N(Ar") 2、N(R 2) 2、C(=O)Ar"、C(=O)R 2、P(=O)(Ar") 2、P(Ar") 2、B(Ar") 2、B(R 2) 2、C(Ar") 3、C(R 2) 3、Si(Ar") 3、Si(R 2) 3、具有1至40個碳原子的直鏈烷基、烷氧基或硫烷氧基或具有3至40個碳原子的支鏈或環狀烷基、烷氧基或硫烷氧基或具有2至40個碳原子的烯基，每一該等基團可經一或多個R 2基團取代，其中一或多個不相鄰的CH 2基團可經-R 2C=CR 2-、-C≡C-、Si(R 2) 2、C=O、C=S、C=Se、C=NR 2、-C(=O)O-、-C(=O)NR 2-、NR 2、P(=O)(R 2)、-O-、-S-、SO或SO 2置換且其中一或多個氫原子可經D、F、Cl、Br、I、CN或NO 2置換、或具有5至60個芳族環原子的芳族或雜芳族環系統，每一該等基團可經一或多個R 2基團取代、或具有5至60個芳族環原子且可經一或多個R 2基團取代之芳氧基或雜芳氧基、或具有5至60個芳族環原子且可經一或多個R 2基團取代之芳烷基或雜芳烷基、或該等系統之組合；同時，二或更多個較佳地相鄰的R 1基團可一起形成環系統；同時，一或多個R 1基團可與化合物的其他部分形成環系統； Ar"  在各情況下為相同的或不同的且為具有5至30個芳族環原子且可經一或多個R 2基團取代之芳族或雜芳族環系統；同時，與相同的碳原子、矽原子、氮原子、磷原子或硼原子鍵結之兩個Ar''基團亦有可能經由單鍵之橋或選自下列之橋接合在一起：B(R 2)、C(R 2) 2、Si(R 2) 2、C=O、C=NR 2、C=C(R 2) 2、O、S、S=O、SO 2、N(R 2)、P(R 2)和P(=O)R 2； R 2在各情況下為相同的或不同的且選自由下列所組成之群組：H、D、F、CN、具有1至20個碳原子的脂族烴基、或具有5至30個芳族環原子的芳族或雜芳族環系統，且其中一或多個氫原子可經D、F、Cl、Br、I或CN置換，且其可經一或多個各具有1至4個碳原子的烷基取代；同時，二或更多個較佳地相鄰的取代基R 2可一起形成環系統； 排除式(A)、(B)和(C)化合物之保護
Figure 02_image005
。 排除式(A)、(B)和(C)化合物之保護。具有CAS No. 125213-40-3之化合物(A)、具有CAS No. 131847-09-1之化合物(B)及具有CAS No. 166042-85-9之化合物(C)係自先前技術已知，但是其不用於電子裝置中。 在本發明之上下文中的芳基含有6至40個碳原子；在本發明之上下文中的雜芳基含有2至40個碳原子及至少一種雜原子，先決條件為碳原子與雜原子的總數目為至少5。雜原子較佳地選自N、O及/或S。應理解芳基或雜芳基在此意指簡單芳族環，亦即苯，或簡單雜芳族環，例如吡啶、嘧啶或噻吩等，或稠合(縮合)芳基或雜芳基，例如萘、蒽、菲、喹啉、異喹啉等。相比之下，以單一鍵彼此接合之芳族系統(例如聯苯)不稱為芳基或雜芳基，但稱為芳族環系統。 在本發明之上下文中的缺電子雜芳基為具有至少一個雜芳族六員環之雜芳基，該環具有至少一個氮原子。其他的芳族或雜芳族五員環或六員環可稠合至此六員環上。缺電子雜芳基的實例為吡啶、嘧啶、吡𠯤、嗒𠯤、三𠯤、喹啉、喹唑啉或喹㗁啉。 在本發明之上下文中的芳族環系統含有6至60個碳原子於環系統中。在本發明之上下文中的雜芳族環系統含有2至60個碳原子及至少一個雜原子於環系統中，先決條件為碳原子與雜原子的總數目為至少5。雜原子較佳地選自N、O及/或S。應理解在本發明之上下文中的芳族或雜芳族環系統意指不一定僅含有芳基或雜芳基之系統，但其中二或更多個芳基或雜芳基亦有可能以非芳族單元(例如碳、氮或氧原子)接合。例如，諸如茀、9,9'-螺二茀、9,9-二芳基茀、三芳基胺、二芳基醚、茋等之系統亦應視為本發明之上下文中的芳族環系統，且同樣為其中二或更多個芳基例如以低碳烷基接合之系統。芳族環系統較佳地選自茀、9,9'-螺二茀、9,9-二芳基胺或其中二或更多個芳基及/或雜芳基係以單一鍵彼此接合之基團。 在本發明之上下文中，較佳地應理解可含有1至20個碳原子且其中個別的氫原子或CH 2基團亦可經上述基團取代之脂族烴基或烷基或烯基或炔基意指甲基、乙基、正丙基、異丙基、正丁基、異丁基、二級丁基、三級丁基、2-甲基丁基、正戊基、二級戊基、新戊基、環戊基、正己基、新己基、環己基、正庚基、環庚基、正辛基、環辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、環戊烯基、己烯基、環己烯基、庚烯基、環庚烯基、辛烯基、環辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。較佳地應理解具有1至40個碳原子的烷氧基意指甲氧基、三氟甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、二級丁氧基、三級丁氧基、正戊氧基、二級戊氧基、2‑甲基­丁氧基、正己氧基、環己氧基、正庚氧基、環庚氧基、正辛氧基、環辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基。應理解具有1至40個碳原子的烷硫基(thioalkyl)尤其意指甲硫基、乙硫基、正丙硫基、異丙硫基、正丁硫基、異丁硫基、二級丁硫基、三級丁硫基、正戊硫基、二級戊硫基、正己硫基、環己硫基、正庚硫基、環庚硫基、正辛硫基、環辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、環戊烯硫基、己烯硫基、環己烯硫基、庚烯硫基、環庚烯硫基、辛烯硫基、環辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基。根據本發明之烷基、烷氧基或烷硫基通常可為直鏈、支鏈或環狀，其中一或多個不相鄰的CH 2基團可經上述基團置換；另外，一或多個氫原子亦有可能經D、F、Cl、Br、I、CN或NO 2，較佳地經F、Cl或CN，更佳地經F或CN，尤佳地經CN置換。 應理解具有5至60個或5至40個芳族環原子，且亦可在各例子中經上述基團取代且可經由任何所欲位置接合至芳族或雜芳族系統之芳族或雜芳族環系統尤其意指自下列所衍生之基團：苯、萘、蒽、苯并蒽、菲、芘、䓛(chrysene)、苝、丙二烯合茀(fluoranthene)、稠四苯、稠五苯、苯并芘、聯苯、聯伸苯(biphenylene)、聯三苯、聯伸三苯(triphenylene)、茀、螺二茀、二氫菲、二氫芘、四氫芘、順-或反-茚并茀、順-或反-茚并咔唑、順-或反-吲哚并咔唑、三聚茚(truxene)、異三聚茚(isotruxene)、螺三聚茚、螺異三聚茚、呋喃、苯并呋喃、異苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、異苯并噻吩、二苯并噻吩、吡咯、吲哚、異吲哚、咔唑、吡啶、喹啉、異喹啉、吖啶、啡啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、啡噻𠯤、啡㗁𠯤、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑(naphthimidazole)、菲并咪唑(phenanthrimidazole)、吡啶并咪唑(pyridimidazole)、吡𠯤并咪唑(pyrazinimidazole)、喹㗁啉并咪唑(quinoxalinimidazole)、㗁唑、苯并㗁唑、苯并㗁唑、萘并㗁唑(naphthoxazole)、蒽并㗁唑(anthroxazole)、菲并㗁唑(phenanthroxazole)、異㗁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、嗒𠯤、六氮雜聯伸三苯、苯并嗒𠯤、嘧啶、苯并嘧啶、喹㗁啉、1,5-二氮雜蒽、2,7-二氮雜芘、2,3-二氮雜芘、1,6-二氮雜芘、1,8-二氮雜芘、4,5-二氮雜芘、4,5,9,10-四氮雜苝、吡𠯤、啡𠯤、啡㗁𠯤、啡噻𠯤、螢紅環(fluorubin)、㖠啶、氮雜咔唑、苯并咔啉、啡啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-㗁二唑、1,2,4-㗁二唑、1,2,5-㗁二唑、1,3,4-㗁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三𠯤、1,2,4-三𠯤、1,2,3-三𠯤、四唑、1,2,4,5-四𠯤、1,2,3,4-四𠯤、1,2,3,5-四𠯤、嘌呤、喋啶、吲巾和苯并噻二唑，或自該等系統之組合所衍生之基團。 在本發明說明之上下文中，應理解二或更多個基團可一起形成環的用辭尤其意指兩個基團係藉由化學鍵以形式上消除兩個氫原子而彼此接合。這由以下圖解例證：
Figure 02_image007
。 然而，另外亦應理解上述用辭意指若兩個基團中之一者為氫，則第二基團係結合至與氫原子鍵結之位置以形成環。這將由以下圖解例證：
Figure 02_image009
。 在較佳的組態中，本發明化合物可包含式(II-1)至(II-42)之結構；本發明化合物更佳地可選自式(II-1)至(II-42)化合物：
Figure 02_image011
Figure 02_image013
Figure 02_image015
Figure 02_image017
Figure 02_image019
Figure 02_image021
Figure 02_image023
Figure 02_image025
Figure 02_image027
Figure 02_image029
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Figure 02_image033
Figure 02_image035
Figure 02_image037
Figure 02_image039
Figure 02_image041
Figure 02_image043
Figure 02_image045
Figure 02_image047
Figure 02_image049
Figure 02_image051
Figure 02_image053
Figure 02_image055
Figure 02_image057
Figure 02_image059
Figure 02_image061
Figure 02_image063
Figure 02_image065
Figure 02_image067
Figure 02_image069
Figure 02_image071
Figure 02_image073
Figure 02_image075
Figure 02_image077
Figure 02_image079
Figure 02_image081
Figure 02_image083
Figure 02_image085
Figure 02_image087
Figure 02_image089
Figure 02_image091
Figure 02_image093
其中符號W a和W b具有上文，尤其以式(I)給出之定義，且其他符號係如下： Y a在各情況下為相同的或不同的且為N(Ar)、N(R a)、P(Ar)、P(R a)、P(=O)Ar、P(=O)R a、P(=S)Ar、P(=S)R a、B(Ar)、B(R a)、Al(Ar)、Al(R a)、Ga(Ar)、Ga(R a)、C=O、C(R a) 2、Si(R a) 2、Ge(R a) 2、C=NR a、C=NAr、C=C(R a) 2、C=C(R a)(Ar)、O、S、Se、S=O或SO 2，較佳為N(Ar)、N(R a)、B(Ar)、B(R a)、P(=O)R a、P(=O)Ar、C=O、C(R a) 2、C=C(R a) 2、C=C(R a)(Ar)、Si(R a) 2、O、S、Se、S=O或SO 2，更佳為N(Ar)、C(R a) 2、O或S，其中R a具有上文，尤其以式(I)詳述之定義； Y b在各情況下為相同的或不同的且為N(Ar)、N(R b)、P(Ar)、P(R b)、P(=O)Ar、P(=O)R b、P(=S)Ar、P(=S)R b、B(Ar)、B(R b)、Al(Ar)、Al(R a)、Ga(Ar)、Ga(R b)、C=O、C(R b) 2、Si(R b) 2、Ge(R b) 2、C=NR b、C=NAr、C=C(R b) 2、C=C(R b)(Ar)、O、S、Se、S=O或SO 2，較佳為N(Ar)、N(R b)、B(Ar)、B(R b)、P(=O)R b、P(=O)Ar、C=O、C(R b) 2、C=C(R b) 2、C=C(R b)(Ar)、Si(R b) 2、O、S、Se、S=O或SO 2，更佳為N(Ar)、C(R b) 2、O或S，其中R b具有上文，尤其以式(I)詳述之定義； Y 1、Y 2在各情況下為相同的或不同的且為N(Ar)、N(R)、P(Ar)、P(R)、P(=O)Ar、P(=O)R、P(=S)Ar、P(=S)R、B(Ar)、B(R)、Al(Ar)、Al(R)、Ga(Ar)、Ga(R)、C=O、C(R) 2、Si(R) 2、Ge(R) 2、C=NR、C=NAr、C=C(R) 2、C=C(R)(Ar)、O、S、Se、S=O或SO 2，較佳為N(Ar)、N(R)、B(Ar)、B(R)、P(=O)R、P(=O)Ar、C=O、C(R) 2、C=C(R) 2、C=C(R)(Ar)、Si(R) 2、O、S、Se、S=O或SO 2，更佳為N(Ar)、C(R) 2、O或S，其中R具有上文，尤其以式(I)詳述之定義； X    在各情況下為相同的或不同的且為N或CR，較佳為CR，先決條件為在一個環中的X基團不超過兩個為N，其中R具有上文，尤其以式(I)詳述之定義； X a在各情況下為相同的或不同的且為N或CR a，較佳為CR a，先決條件為在一個環中的X a基團不超過兩個為N，其中R a具有上文，尤其以式(I)詳述之定義； X b在各情況下為相同的或不同的且為N或CR b，較佳為CR b，先決條件為在一個環中的X b基團不超過兩個為N，其中R b具有上文，尤其以式(I)詳述之定義。 在此優先選擇為式(II-1)至(II-31)之結構，且特別優先選擇為式(II-1)至(II-4)、(II-6)、(II-8)、(II-10)、(II-12)、(II-14)、(II-16)至(II-19)、(II-21)、(II-23)、(II-25)、(II-27)、(II-29)、(II-31)之結構。 另外，尤其優先選擇為包括式(I)及(II-1)至(II-42)之結構之化合物，W a、W b基團中至少一者為O；較佳以兩個W a、W b基團皆為O。 若二或更多個氮原子存在於化合物中，則該等氮原子較佳地不相鄰且因此沒有N-N鍵存在。 在進一步較佳的實施態樣中，可能為以下例子：本發明化合物包括式(III-1)至(III-41)之結構，其中本發明化合物可更佳地選自式(III-1)至(III-41)化合物
Figure 02_image095
Figure 02_image097
Figure 02_image099
Figure 02_image101
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其中符號Y 1、Y 2、Y a、Y b、X、X a和X b具有上文，尤其以式(II-1)至(II-42)給出之意義。 在此優先選擇為式(III-1)至(III-31)之結構，且特別優先選擇為式(III-1)至(III-4)、(III-6)、(III-8)、(III-10)、(III-12)、(III-14)、(III-16)至(III-19)、(III-21)、(III-23)、(III-25)、(III-27)、(III-29)、(III-31)之結構。 較佳地可能為以下例子：在式(II-1)至(II-42)及/或(III-1)至(III-41)中，不超過四個，且較佳地不超過兩個X、X a和X b基團為N；更佳地全部的X、X a和X b基團皆為CR、CR a或CR b。 在進一步較佳的實施態樣中，可能為以下例子：本發明化合物包括式(IV-1)至(IV-41)之結構，其中本發明化合物可更佳地選自式(IV-1)至(IV-41)化合物。
Figure 02_image177
Figure 02_image179
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Figure 02_image257
其中符號R、R a和R b具有上文，尤其以式(I)給出之定義，符號Y 1、Y 2、Y a和Y b具有上文，尤其以式(II-1)至(II-42)給出之意義，且其他符號具有以下定義： m    為0、1、2、3或4，較佳為0、1或2； j     為0、1或2，較佳為0或1。 在此優先選擇為式(IV-1)至(IV-31)之結構/化合物，且特別優先選擇為式(IV-1)至(IV-4)、(IV-6)、(IV-8)、(IV-10)、(IV-12)、(IV-14)、(IV-16)至(IV-19)、(IV-21)、(IV-23)、(IV-25)、(IV-27)、(IV-29)、(IV-31)之結構/化合物。 可能進一步為以下例子：Y a和Y b基團為相同的。另外，Y a和Y b基團可為不相同的。 在進一步的組態中，可能為以下例子：Y a和Y b基團中之一者為O，及Y a和Y b基團中之一者為C(R a) 2或C(R b) 2。 在進一步的實施態樣中，可能為以下例子：Y a和Y b基團中之一者為Nar，及Y a和Y b基團中之一者為C(R a) 2或C(R b) 2。 亦可能為以下例子：Y 1和Y 2基團為相同的。另外，Y 1和Y 2基團可為不相同的。 在進一步的組態中，可能為以下例子：Y 1和Y 2基團中之一者為O，及Y 1和Y 2基團中之一者為C(R a) 2或C(R b) 2。 在進一步的實施態樣中，可能為以下例子：Y 1和Y 2基團中之一者為NAr，及Y 1和Y 2基團中之一者為C(R a) 2或C(R b) 2。 在進一步較佳的實施態樣中，可能為以下例子：本發明化合物包括式(V-1)至(V-8)之結構，其中本發明化合物可更佳地選自式(V-1)至(V-8)化合物
Figure 02_image259
Figure 02_image261
Figure 02_image263
Figure 02_image265
其中符號R a和R b具有上文，尤其以式(I)給出之定義，且其他符號具有以下定義： R c、R d在各情況下為相同的或不同的且為N(Ar') 2、N(R 1) 2、C(=O)N(Ar') 2、C(=O)N(R 1) 2、C(Ar') 3、C(R 1) 3、Si(Ar') 3、Si(R 1) 3、B(Ar') 2、B(R 1) 2、C(=O)Ar'、C(=O)R 1、P(=O)(Ar') 2、P(=O)(R 1) 2、P(Ar') 2、P(R 1) 2、S(=O)Ar'、S(=O)R 1、S(=O) 2Ar'、S(=O) 2R 1、OSO 2Ar'、OSO 2R 1、具有1至40個碳原子的直鏈烷基、烷氧基或硫烷氧基或具有2至40個碳原子的烯基或炔基、或具有3至20個碳原子的支鏈或環狀烷基、烷氧基或硫烷氧基，其中該等烷基、烷氧基、硫烷氧基、烯基或炔基可在各例子中經一或多個R 1基團取代，其中一或多個不相鄰的CH 2基團可經R 1C=CR 1、C≡C、Si(R 1) 2、C=O、C=S、C=Se、C=NR 1、-C(=O)O-、-C(=O)NR 1-、NR 1、P(=O)(R 1)、 -O-、-S-、SO或SO 2置換、或具有5至60個芳族環原子且可在各例子中經一或多個R 1基團取代之芳族或雜芳族環系統、或具有5至60個芳族環原子且可經一或多個R 1基團取代之芳氧基或雜芳氧基、或具有5至60個芳族環原子且可經一或多個R 1基團取代之雜芳硫基、或具有5至60個芳族環原子且可經一或多個R 1基團取代之二芳胺基、芳基雜芳胺基、二雜芳胺基、或具有5至60個芳族環原子及在烷基中的1至10個碳原子且可經一或多個R 1基團取代之芳基烷基或雜芳基烷基；同時，一個R c基團可與R、R a、R b、R d基團或另一基團形成環系統；同時，R d基團可與R、R a、R b、R c基團或另一基團形成環系統； m    為0、1、2、3或4，較佳為0、1或2； n    為0、1、2或3，較佳為0、1或2。 另外，尤其關於式(V-1)至(V-8)之結構/化合物，可能為以下例子：R c和R d基團為相同的。另外，R c和R d基團可為不同的。 標號j、m及n之總和(尤其在式(IV-1)至(IV-41)及/或(V-1)至(V-8)之結構/化合物中)較佳為最多10，較佳為不超過8，尤佳為不超過6，且更佳為不超過4。 另外，在包括(I)、(II-1)至(II-42)、(III-1)至(III-42)、(IV-1)至(IV-41)、(V-1)至(V-8)之式及/或下文詳述的該等式之較佳的實施態樣中，可能為以下例子：至少一個R、R a、R b、R c、R d基團為具有1至40個碳原子的直鏈烷基、烷氧基或硫烷氧基、或具有2至40個碳原子的烯基或炔基、或具有3至20個碳原子的支鏈或環狀烷基、烷氧基或硫烷氧基，其中該等烷基、烷氧基、硫烷氧基、烯基或炔基可在各例子中經一或多個R 1基團取代，其中一或多個不相鄰的CH 2基團可經R 1C=CR 1、C≡C、Si(R 1) 2、C=O、C=S、C=Se、C=NR 1、-C(=O)O-、-C(=O)NR 1-、NR 1、P(=O)(R 1)、-O-、-S-、SO或SO 2置換、或為具有5至60個芳族環原子且可在各例子中經一或多個R 1基團取代之芳族或雜芳族環系統、或為具有5至60個芳族環原子且可經一或多個R 1基團取代之芳基或雜芳氧基、或為具有5至60個芳族環原子且可經一或多個R 1基團取代之雜芳硫基、或為具有5至60個芳族環原子且可經一或多個R 1基團取代之二芳胺基、芳基雜芳胺基、二雜芳胺基、或為具有5至60個芳族環原子及在烷基中的1至10個碳原子且可經一或多個R 1基團取代之芳基烷基或雜芳基烷基。 在包括(I)、(II-1)至(II-42)、(III-1)至(III-42)、(IV-1)至(IV-41)、(V-1)至(V-8)之式及/或下文詳述的該等式之較佳的實施態樣中，較佳地可能為以下例子：至少一個R、R a、R b、R c、R d基團為具有5至60個芳族環原子且可在各例子中經一或多個R 1基團取代之芳族或雜芳族環系統、或為具有5至60個芳族環原子且可經一或多個R 1基團取代之芳基或雜芳氧基、或為具有5至60個芳族環原子且可經一或多個R 1基團取代之雜芳硫基、或為具有5至60個芳族環原子且可經一或多個R 1基團取代之二芳胺基、芳基雜芳胺基、二雜芳胺基、或為具有5至60個芳族環原子及在烷基中的1至10個碳原子且可經一或多個R 1基團取代之芳基烷基或雜芳基烷基，更佳為具有5至60個芳族環原子且可在各例子中經一或多個R 1基團取代之芳族或雜芳族環系統。 在本發明之較佳發展中，可能為以下例子：至少兩個R、R a、R b、R c、R d基團與該兩個R、R a、R b、R c、R d基團結合之其他基團一起形成稠合環，其中兩個R、R a、R b、R c、R d基團形成至少一個式(RA-1)至(RA-12)之結構：
Figure 02_image267
Figure 02_image269
Figure 02_image271
Figure 02_image273
其中R 1具有上文詳述之定義，虛線鍵表示連接位點，兩個R、R a、R b、R c、R d基團經由其結合至其他基團，且其他符號具有以下定義： Y 3在各情況下為相同的或不同的且為C(R 1) 2、 (R 1) 2C-C(R 1) 2、(R 1)C=C(R 1)、NR 1、NAr'、O或S，較佳為C(R 1) 2、(R 1) 2C-C(R 1) 2、(R 1)C=C(R 1)、O或S； R e在各情況下為相同的或不同的且為F、具有1至40個碳原子的直鏈烷基、烷氧基或硫烷氧基、或具有2至40個碳原子的烯基或炔基、或具有3至20個碳原子的支鏈或環狀烷基、烷氧基或硫烷氧基，其中該等烷基、烷氧基、硫烷氧基、烯基或炔基可在各例子中經一或多個R 2基團取代，其中一或多個相鄰的CH 2基團可經R 2C=CR 2、C≡C、Si(R 2) 2、C=O、C=S、C=Se、C=NR 2、-C(=O)O-、-C(=O)NR 2-、NR 2、P(=O)(R 1)、 -O-、-S-、SO或SO 2置換、或具有5至60個芳族環原子且可在各例子中經一或多個R 2基團取代之芳族或雜芳族環系統、或具有5至60個芳族環原子且可經一或多個R 2基團取代之芳氧基或雜芳氧基；同時，亦有可能使兩個R e基團一起或一個R e基團與R 1基團一起或與另一基團一起形成環系統； s     為0、1、2、3、4、5或6，較佳為0、1、2、3或4，更佳為0、1或2； t     為0、1、2、3、4、5、6、7或8，較佳為0、1、2、3或4，更佳為0、1或2； v    為0、1、2、3、4、5、6、7、8或9，較佳為0、1、2、3或4，更佳為0、1或2。 在本發明之較佳的實施態樣中，至少兩個R、R a、R b、R c、R d基團與該兩個R、R a、R b、R c、R d基團結合之其他基團一起形成稠合環，其中兩個R、R a、R b、R c、R d基團較佳地形成式(RA-1a)至(RA-4f)之結構中至少一者：
Figure 02_image275
Figure 02_image277
其中虛線鍵表示連接位點，兩個R、R a、R b、R c、R d基團係經由其結合至其他基團，標號m為0、1、2、3或4，較佳為0、1或2，且符號R 1、R 2、R e及標號s和t具有上文，尤其以式(I)及/或式(RA-1)至(RA-12)詳述之定義。 可能進一步為以下例子：至少兩個R、R a、R b、R c、R d基團形成式(RA-1)至(RA-12)及/或(RA-1a)至(RA-4f)之結構且形成稠合環、表示來自相鄰的X、X a、X b基團之R、R a、R b、R c、R d基團、或表示分別結合至相鄰的碳原子之R、R a、R b、R c、R d基團，其中該等碳原子較佳地經由鍵連接。 在進一步較佳的組態中，至少兩個R、R a、R b、R c、R d基團與該兩個R、R a、R b、R c、R d基團結合之其他基團一起形成稠合環，其中兩個R、R a、R b、R c、R d基團形成式(RB)之結構，
Figure 02_image279
其中R 1具有上文，尤其以式(I)闡述之定義，虛線鍵表示鍵結位點，兩個R、R a、R b、R c、R d基團係經由其結合至其他基團，標號m為0、1、2、3或4，較佳為0、1或2，且Y 4為C(R 1) 2、NR 1、NAr'、BR 1、BAr'、O或S，較佳為C(R 1) 2、NAr'或O。 在此可能為以下例子：至少兩個R、R a、R b、R c、R d基團形成式(RB)之結構且形成稠合環、表示來自相鄰的X、X a、X b基團之R、R a、R b、R c、R d基團、或表示分別結合至相鄰的碳原子之R、R a、R b、R c、R d基團，其中該等碳原子較佳地經由鍵連接。 化合物更佳地包括至少一個式(VI-1)至(VI-22)之結構；化合物更佳地選自式(VI-1)至(VI-22)化合物，其中化合物具有至少一個稠合環：
Figure 02_image281
Figure 02_image283
Figure 02_image285
其中符號R、R a、R b、Y 1和Y 2具有上文，尤其以式(I)及/或式(II-1)至(II-42)給出之定義，符號o表示連接位點，且其他符號具有以下定義： m    為0、1、2、3或4，較佳為0、1或2； j     為0、1或2，較佳為0或1； k    為0或1。 在此優先選擇為式(VI-1)至(VI-4)之結構/化合物。 化合物更佳地包括至少一個式(VII-1)至(VII-4)之結構；化合物更佳地選自式(VII-1)至(VII-4)化合物，其中化合物具有至少一個稠合環：
Figure 02_image287
其中符號R、R a和R b具有上文，尤其以式(I)給出之定義，符號o表示稠合環之連接位點，且其他符號具有以下定義： j     為0、1或2，較佳為0或1； k    為0或1。 稠合環(尤其在式(VI-1)至(VI-22)及/或(VII-1)至(VII-4)中)較佳地由至少兩個R、R a、R b、R c、R d基團及與該兩個R、R a、R b、R c、R d基團結合之其他基團形成，其中至少兩個R、R a、R b、R c、R d基團形成式(RA-1)至(RA-12)及/或式(RB)之結構，較佳為式(RA-1)至(RA-12)之結構。 較佳地可能為以下例子：化合物具有至少兩個稠合環，其中至少一個稠合環係由式(RA-1)至(RA-12)及/或(RA-1a)至(RA-4f)之結構形成及另一環係由式(RA-1)至(RA-12)、(RA-1a)至(RA-4f)或(RB)之結構形成。 尤其在式(VI-1)至(VI-22)及/或(VII-1)至(VII-4)中，標號k、j和m的總和較佳為0、1、2或3，更佳為1或2。 另外可能為以下例子：根據上式之取代基R、R a、R b、R c、R d、R e、R 1和R 2不與該取代基R、R a、R b、R c、R d、R e、R 1和R 2結合之環系統的環原形成稠合芳族或雜芳族環系統。這包括與可與R、R a、R b、R c、R d、R e和R 1基團鍵結之可能的取代基形成稠合芳族或雜芳族環系統。 當兩個尤其可選自R、R a、R b、R c、R d、R e、R 1及/或R 2的基團彼此形成環系統時，此環系統可為單或多環、脂族、雜脂族、芳族或雜芳族。在此例子中，一起形成環系統的基團可為相鄰的，其意指該等基團係與同一碳原子或與彼此直接鍵結的碳原子鍵結，或該等基團可進一步自彼此去除。另外，具備有取代基R、R a、R b、R c、R d、R e、R 1及/或R 2之環系統亦可經由鍵彼此接合，使得此可造成環閉合。在此例子中，每一對應的鍵結位點較佳地具備有取代基R、R a、R b、R c、R d、R e、R 1及/或R 2。 在較佳的組態中，本發明化合物可以式(I)、(II-1)至(II-42)、(III-1)至(III-42)、(IV-1)至(IV-41)、(V-1)至(V-8)、(VI-1)至(VI-22)及/或(VII-1)至(VII-4)之結構中至少一者表示。較佳地包含式(I)、(II-1)至(II-42)、(III-1)至(III-42)、(IV-1)至(IV-41)、(V-1)至(V-8)、(VI-1)至(VI-22)及/或(VII-1)至(VII-4)之結構的本發明化合物較佳地具有不超過5000 g/mol，較佳為不超過4000 g/mol，特佳為不超過3000 g/mol，尤佳為不超過2000 g/mol，且最佳為不超過1200 g/mol之分子量。 另外，較佳的本發明化合物之特性在與彼等為可昇華的。該等化合物通常具有少於約1200 g/mol之莫耳質量。 較佳的芳族或雜芳族環系統R、R a、R b、R c、R d、R e、Ar'及/或Ar係選自苯基、聯苯(尤其為鄰-、間-或對-聯苯)、聯三苯(尤其為鄰-、間-或對-聯三苯或支鏈聯三苯)、聯四苯(尤其為鄰-、間-或對-聯四苯或支鏈聯四苯)、可經由1、2、3或4位置接合之茀、可經由1、2、3或4位置接合之螺二茀、萘(尤其為經1-或2-鍵結之萘)、吲哚、苯并呋喃、苯并噻吩、可經由1、2、3、4或9位置接合之咔唑、可經由1、2、3或4位置接合之二苯并呋喃、可經由1、2、3或4位置接合之二苯并噻吩、茚并咔唑、吲哚并咔唑、吡啶、嘧啶、吡𠯤、嗒𠯤、三𠯤、喹啉、異喹啉、喹唑啉、喹㗁啉、菲或聯伸三苯，每一該等可經一或多個R 1或R基團取代。 較佳地可能為以下例子：至少一個取代基R、R a、R b在各情況下為相同的或不同的且選自由下列所組成之群組：H、D、具有3至20個碳原子的支鏈或環狀烷基、烷氧基或硫烷氧基、或選自下式Ar-1至Ar-78之群組的芳族或雜芳族環系統；取代基R、R a、R b較佳地形成較佳地根據式(RA-1)至(RA-12)或(RB)之結構的稠合環，或取代基R、R a、R b在各情況下為相同的或不同的且選自由下列所組成之群組：H、D或選自下式Ar-1至Ar-78之群組的芳族或雜芳族環系統，及/或Ar'基團在各情況下為相同的或不同的且選自下式Ar-1至Ar-78之群組：
Figure 02_image289
Figure 02_image291
Figure 02_image293
Figure 02_image295
Figure 02_image297
Figure 02_image299
Figure 02_image301
Figure 02_image303
其中R 1係如有上文所定義，虛線鍵表示連接位點，且另外： Ar 1在各情況下為相同的或不同的且為具有6至18個芳族環原子且可在各例子中經一或多個R 1基團取代之二價芳族或雜芳族環系統； A    在各情況下為相同的或不同的且為C(R 1) 2、NR 1、O或S； p    為0或1，其中p=0意指Ar 1基團不存在且對應的芳族或雜芳族基團係直接鍵結至對應基團； q    為0或1，其中q=0意指沒有A基團在此位置上鍵結，且R 1基團反而鍵結至對應的碳原子。 在此優先選擇為式(Ar-1)、(Ar-2)、(Ar-3)、(Ar-12)、(Ar-13)、(Ar-14)、(Ar-15)、(Ar-16)、(Ar-40)、(Ar-41)、(Ar-42)、(Ar-43)、(Ar-45)、(Ar-47)、(Ar-57)、(Ar-69)、(Ar-70)、(Ar-75)、(Ar-78)之結構，且特別優先選擇為式(Ar-1)、(Ar-2)、(Ar-3)、(Ar-12)、(Ar-13)、(Ar-14)、(Ar-15)、(Ar-16)之結構。 當式(Ar-1)至(Ar-78)之結構的前述基團具有二或更多個A基團時，該等基團的可能選擇包括來自A之定義的所有組合。在此例子中，較佳的實施態樣為那些其中一個A基團為NR 1及其他A基團為C(R 1) 2，或其中兩個A基團為NR 1，或其中兩個A基團為O。 當A為NR 1時，與氮原子鍵結之取代基R 1較佳為具有5至24個芳族環原子且亦可經一或多個R 2基團取代之芳族或雜芳族環系統。在特佳的實施態樣中，此R 1取代基在各情況下為相同的或不同的且為具有6至24個芳族環原子，尤其為6至18個芳族環原子的芳族或雜芳族環系統，其不具有其中二或更多個芳族或雜芳族6員環基團彼此直接稠合的任何稠合芳基及任何稠合雜芳基，且其亦可在各例子中經一或多個R 2基團取代。優先選擇為具有如上文以Ar-1至Ar-11列出之鍵結模式的苯基、聯苯、聯三苯和聯四苯，其中該等結構可經一或多個R 2基團而非R 1取代，但較佳地未經取代。進一步優先選擇為如上文以Ar-47至Ar-50、Ar-57和Ar-58列出之三𠯤、嘧啶和喹唑啉，其中該等結構可經一或多個R 2基團而非R 1取代。 隨後說明較佳的取代基R、R a、R b、R c、R d和R e。 在本發明之較佳的實施態樣中，R、R a、R b在各情況下為相同的或不同的且選自由下列所組成之群組：H、D、F、CN、NO 2、Si(R 1) 3、B(OR 1) 2、具有1至20個碳原子的直鏈烷基或具有3至20個碳原子的支鏈或環狀烷基，其中該烷基可在各例子中經一或多個R 1基團取代、或具有5至60個芳族環原子，較佳為5至40個芳族環原子且可在各例子中經一或多個R 1基團取代之芳族或雜芳族環系統。 在本發明之進一步較佳的實施態樣中，取代基R、R a、R b在各情況下為相同的或不同的且選自由下列所組成之群組：H、D、F、具有1至20個碳原子的直鏈烷基或具有3至20個碳原子的支鏈或環狀烷基，其中該烷基可在各例子中經一或多個R 1基團取代、或具有5至60個芳族環原子，較佳為5至40個芳族環原子且可在各例子中經一或多個R 1基團取代之芳族或雜芳族環系統。 可能進一步為以下例子：至少一個取代基R、R a、R b在各情況下為相同的或不同的且選自由下列所組成之群組：H、D、具有6至30個芳族環原子且可經一或多個R 1基團取代之芳族或雜芳族環系統、或N(Ar') 2基團。在本發明之進一步較佳的實施態樣中，取代基R、R a、R b、R c、R d形成根據式(RA-1)至(RA-12)、(RA-1a)至(RA-4f)或(RB)之結構的環，或R、R a、R b在各情況下為相同的或不同的且選自由下列所組成之群組：H、D、具有6至30個芳族環原子且可經一或多個R 1基團取代之芳族或雜芳族環系統、或N(Ar') 2基團。取代基R、R a、R b更佳地在各情況下為相同的或不同的且選自由下列所組成之群組：H或具有6至24個芳族環原子，較佳為具有6至18個芳族環原子，更佳為具有6至13個芳族環原子的芳族或雜芳族系統，每一該等可經一或多個R 1基團取代。 較佳地可能為以下例子：至少一個取代基R、R a、R b、R c、R d係選自苯基、聯苯、聯三苯、聯四苯、茀、螺二茀、萘、吲哚、苯并呋喃、苯并噻吩、咔唑、二苯并呋喃、二苯并噻吩、茚并咔唑、吲哚并咔唑、吡啶、嘧啶、吡𠯤、嗒𠯤、三𠯤、喹啉、異喹啉、喹唑啉、喹㗁啉、菲和聯伸三苯，每一該等可經一或多個R 1基團取代。在此更特別地以語詞「取代基」意味著R、R a、R b、R c、R d不為H。另外，若有二或更多個選自所述及之芳族或雜芳族基團的取代基存在，則取代基R、R a、R b、R c、R d可為相同的或不同的。 在進一步的實施態樣中，可能為以下例子：至少一個取代基R、R a、R b、R c、R d係選自o-聯苯、o,o'-聯三苯、o,o',p-聯四苯、4,6-二苯基嘧啶-2-基、4,6-二苯基三𠯤-2-基、萘、菲、䓛、螺二茀、聯伸三苯、蒽、苯并蒽、茀及/或芘，每一該等可經一或多個R 1基團取代。在此優先選擇為螺二茀、o-聯苯、o,o'-聯三苯、o,o',p-聯四苯、4,6-二苯基嘧啶-2-基、4,6-二苯基三𠯤-2-基。若有二或更多個選自所述及之芳族的取代基存在，則取代基R、R a、R b、R c、R d可為相同的或不同的。具有選自o-聯苯、o,o'-聯三苯、o,o',p-聯四苯、4,6-二苯基嘧啶-2-基、4,6-二苯基三𠯤-2-基、萘、菲、䓛、螺二茀、聯伸三苯、蒽、苯并蒽、茀及/或芘之群組的結構/化合物尤其適合用作為電子傳輸材料及/或基質材料。 有關取代基R c、R d，同樣對應地適用如上文關於具有前述限制之取代基R、R a、R b闡述之優先選擇的陳述。尤其可能為以下例子：至少一個取代基R c、R d在各情況下為相同的或不同的且選自由下列所組成之群組：具有6至30個芳族環原子且可經一或多個R 1基團取代之芳族或雜芳族環系統及N(Ar') 2基團。另外可能為以下例子：取代基R c、R d形成較佳地根據式(RA-1)至(RA-12)或(RB)之結構的稠合環，或取代基R c、R d在各情況下為相同的或不同的且選自由下列所組成之群組：具有6至30個芳族環原子且可經一或多個R 1基團取代之芳族或雜芳族環系統及N(Ar') 2基團。 更佳地可能為以下例子：取代基R c、R d在各情況下為相同的或不同的且表示具有6至30個芳族環原子且可經一或多個選自上文所示之式(Ar-1)至(Ar-78)之群組的R 1基團取代之芳族或雜芳族環系統。 在本發明之較佳的實施態樣中，R e在各情況下為相同的或不同的且選自由下列所組成之群組：具有1至20個碳原子的直鏈烷基或具有3至20個碳原子的支鏈或環狀烷基，其中該烷基可在各例子中經一或多個R 1基團取代、或具有5至60個芳族環原子，較佳為5至40個芳族環原子且可在各例子中經一或多個R 2基團取代之芳族或雜芳族環系統。 在本發明之進一步較佳的實施態樣中，R e在各情況下為相同的或不同的且選自由下列所組成之群組：具有1至10個碳原子的直鏈烷基或具有3至10個碳原子的支鏈或環狀烷基，其中該烷基可在各例子中經一或多個R 2基團取代、具有6至30個芳族環原子且可經一或多個R 2基團取代之芳族或雜芳族環系統。R e更佳地在各情況下為相同的或不同的且選自由下列所組成之群組：具有1至5個碳原子的直鏈烷基、或具有3至5個碳原子的支鏈或環狀烷基，其中該烷基可在各例子中經一或多個R 2基團取代、或具有6至24個芳族環原子，較佳為6至18個芳族環原子，更佳為6至13個芳族環原子且可在各例子中經一或多個R 2基團取代之芳族或雜芳族環系統。 在本發明之較佳的實施態樣中，R e在各情況下為相同的或不同的且選自由下列所組成之群組：具有1至6個碳原子的直鏈烷基或具有3至6個碳原子的環狀烷基，其中該烷基可在各例子中經一或多個R 2基團取代、或具有6至24個芳族環原子且可在各例子中經一或多個R 2基團取代之芳族或雜芳族環系統；同時，兩個R e基團亦可一起形成形成環系統。R e更佳地在各情況下為相同的或不同的且選自由下列所組成之群組：具有1、2、3或4個碳原子的直鏈烷基或具有3至6個碳原子的支鏈或環狀烷基，其中該烷基可在各例子中經一或多個R 2基團取代，但較佳地未經取代、或具有6至12個芳族環原子，尤其為6個芳族環原子且可在各例子中經一或多個較佳的非芳族R 2基團取代，但較佳地未經取代之芳族環系統；同時，兩個R e基團可一起形成環系統。R e最佳地在各情況下為相同的或不同的且選自由下列所組成之群組：具有1、2、3或4個碳原子的直鏈烷基或具有3至6個碳原子的支鏈烷基。R e最佳為甲基或苯基，其中兩個苯基可一起形成環系統，優先選擇為甲基而非苯基。 以取代基R、R a、R b、R c、R d、R e或Ar或Ar'表示之較佳的芳族或雜芳族環系統係選自苯基、聯苯(尤其為鄰-、間-或對-聯苯)、聯三苯(尤其為鄰-、間-或對-聯三苯或支鏈聯三苯)、聯四苯(尤其為鄰-、間-或對-聯四苯或支鏈聯四苯)、可經由1、2、3或4位置接合之茀、可經由1、2、3或4位置接合之螺二茀、萘(尤其為經1-或2-鍵結之萘)、吲哚、苯并呋喃、苯并噻吩、可經由1、2、3或4位置接合之咔唑、可經由1、2、3或4位置接合之二苯并呋喃、可經由1、2、3或4位置接合之二苯并噻吩、茚并咔唑、吲哚并咔唑、吡啶、嘧啶、吡𠯤、嗒𠯤、三𠯤、喹啉、異喹啉、喹唑啉、喹㗁啉、菲或聯伸三苯，每一該等可經一或多個R、R 1或R 2基團取代。以上文列出之結構Ar-1至Ar-78特佳，優先選擇為式(Ar-1)、(Ar-2)、(Ar-3)、(Ar-12)、(Ar-13)、(Ar-14)、(Ar-15)、(Ar-16)、(Ar-69)、(Ar-70)、(Ar-75)之結構，且特別優先選擇為式(Ar-1)、(Ar-2)、(Ar-3)、(Ar-12)、(Ar-13)、(Ar-14)、(Ar-15)、(Ar-16)式(Ar-1)、(Ar-2)、(Ar-3)、(Ar-12)、(Ar-13)、(Ar-14)、(Ar-15)、(Ar-16)之結構。關於結構Ar-1至Ar-78，應聲明該等係以取代基R 1顯示。在環系統Ar的例子中，該等取代基R 1應經R置換，且在R e的例子中，該等取代基R 1應經R 2置換。 其他適合的R、R a、R b、R c、R d基團為式 -Ar 4-N(Ar 2)(Ar 3)之基團，其中Ar 2、Ar 3和Ar 4在各情況下為相同的或不同的且為具有5至24個芳族環原子且可在各例子中經一或多個R 1基團取代之芳族或雜芳族環系統。在Ar 2、Ar 3和Ar 4中的芳族環原子總數目在此不超過60，且較佳為不超過40。 在此例子中，Ar 4和Ar 2亦可彼此鍵結及/或Ar 2和Ar 3彼此以選自C(R 1) 2、NR 1、O和S之基團鍵結。較佳地Ar 4和Ar 2彼此接合及Ar 2和Ar 3彼此在相對於連接氮原子之鍵的各自鄰位置上接合。在本發明進一步的實施態樣中，Ar 2、Ar 3和Ar 4基團中沒有一者彼此鍵結。 Ar 4較佳為具有6至24個芳族環原子，較佳為6至12個芳族環原子且可在各例子中經一或多個R 1基團取代之芳族或雜芳族環系統。Ar 4更佳地選自由鄰-、間-或對-伸苯基或鄰-、間-或對-聯苯基所組成之群組，每一該等可經一或多個R 1基團取代，但較佳地未經取代。Ar 4最佳為未經取代之伸苯基。 Ar 2和Ar 3較佳地在各情況下為相同的或不同的且為具有6至24個芳族環原子且可在各例子中經一或多個R 1基團取代之芳族或雜芳族環系統。特佳的Ar 2和Ar 3基團在各情況下為相同的或不同的且選自由下列所組成之群組：苯、鄰-、間-或對-聯苯、鄰-、間-或對-聯三苯或支鏈聯三苯、鄰-、間-或對-聯四苯或支鏈聯四苯、1-、2-、3-或4-茀基、1-、2-、3-或4-螺二茀基、1-或2-萘基、吲哚、苯并呋喃、苯并噻吩、1-、2-、3-或4-咔唑、1-、2-、3-或4-二苯并呋喃、1-、2-、3-或4-二苯并噻吩、茚并咔唑、吲哚并咔唑、2-、3-或4-吡啶、2-、4-或5-嘧啶、吡𠯤、嗒𠯤、三𠯤、菲或聯伸三苯，每一該等可經一或多個R 1基團取代。Ar 2和Ar 3最佳地在各情況下為相同的或不同的且選自下列所組成之群組：苯、聯苯(尤其為鄰-、間-或對-聯苯)、聯三苯(尤其為鄰-、間-或對-聯三苯或支鏈聯三苯)、聯四苯(尤其為鄰-、間-或對-聯四苯或支鏈聯四苯)、茀(尤其為1-、2-、3-或4-茀)或螺二茀(尤其為1-、2-、3-或4-螺二茀)。 在本發明之進一步較佳的實施態樣中，R 1在各情況下為相同的或不同的且選自由下列所組成之群組：H、D、F、CN、具有1至10個碳原子的直鏈烷基或具有3至10個碳原子的支鏈或環狀烷基，其中該烷基可在各例子中經一或多個R 2基團取代、或具有6至24個芳族環原子且可在各例子中經一或多個R 2基團取代之芳族或雜芳族環系統。在本發明之特佳的實施態樣中，R 1在各情況下為相同的或不同的且選自由下列所組成之群組：H、具有1至6個碳原子，尤其為具有1、2、3或4個碳原子的直鏈烷基或具有3至6個碳原子的支鏈或環狀烷基，其中該烷基可經一或多個R 5基團取代，但較佳地未經取代、或具有6至13個芳族環原子且可在各例子中經一或多個R 5基團取代，但較佳地未經取代之芳族或雜芳族環系統。 在本發明之進一步較佳的實施態樣中，R 2在各情況下為相同的或不同的且為H、具有1至4個碳原子的烷基或具有6至10個碳原子的芳基，其可經具有1至4個碳原子的烷基取代，但較佳地未經取代。 同時，在藉由真空蒸發加工之本發明化合物中，烷基較佳地具有不超過5個碳原子，更佳為不超過4個碳原子，最佳為不超過1個碳原子。關於自溶液加工之化合物，適合的化合物亦為那些經具有多達10個碳原子的烷基，尤其為支鏈烷基取代之化合物，或那些經寡伸芳基，例如鄰-、間-或對-聯三苯或支鏈聯三苯或聯四苯基團取代之化合物。 可能進一步為以下例子：化合物包括正好兩個或正好三個式(I)、(II-1)至(II-42)、(III-1)至(III-41)、(IV-1)至(IV-41)、(V-1)至(V-8)、(VI-1)至(VI-22)及/或(VII-1)至(VII-4)之結構。 在較佳的組態中，化合物係選自式(D-1)或(D-2)化合物：
Figure 02_image305
其中L 1基團為連接基團，較佳為鍵或具有5至40個，較佳為5至30個芳族環原子且可經一或多個R 1基團取代之芳族或雜芳族環系統，且所使用之其他符號具有上文，尤其以式(I)給出之定義。 在本發明之進一步較佳的實施態樣中，L 1為鍵或具有5至14個芳族或雜芳族環原子的芳族或雜芳族環系統，較佳為具有6至12個碳原子且可經一或多個R 1基團取代，但較佳地未經取代之芳族環系統，其中R 1可具有上文，尤其以式(I)給出之定義。L 1更佳為具有6至10個芳族環原子的芳族環系統或具有6至13個雜芳族環原子的雜芳族環系統，每一該等可經一或多個R 2基團取代，但較佳地未經取代，其中R 2可具有上文，尤其以式(I)給出之定義。 在式(D2)中所示之符號L 1更佳地在各情況下尤其為相同的或不同的且為鍵或具有5至24個環原子，較佳為6至13個環原子，更佳為6至10個環原子的芳基或雜芳基，使得芳族或雜芳族環系統之芳族或雜芳族基團直接與其他基團的各自原子鍵結，亦即經由芳族或雜芳族基團的原子。 另外可能為以下例子：在式(D2)中所示之L 1基團包含具有不超過四個，較佳為不超過三個，更佳為不超過兩個稠合芳族及/或雜芳族6員環的芳族環系統，且較佳地不包含任何稠合芳族或雜芳族環系統。因此，萘基結構優選於蒽結構。另外，茀基、螺二茀基、二苯并呋喃基及/或二苯并噻吩基結構優選於萘基結構。 特別優先選擇為不具有稠合之結構，例如苯基、聯苯、聯三苯及/或聯四苯結構。 適合的芳族或雜芳族環系統L 1的實例係選自由下列所組成之群組：鄰-、間-或對-伸苯基、鄰-、間-或對-聯伸苯基、聯伸三苯基(尤其為支鏈聯伸三苯基)、聯伸四苯基(尤其為支鏈聯伸四苯基)、伸茀基、伸螺二茀基(spirobifluorenylene)、伸二苯并呋喃基(dibenzofuranylene )、伸二苯并噻吩基(dibenzothienylene)和伸咔唑基(carbazolylene)，每一該等可經一或多個R 1基團取代，但較佳地未經取代。 前述較佳的實施態樣可在請求項1中所定義的限制範圍內依需要彼此組合。在本發明之特佳的實施態樣中，前述優先選擇係同時發生。 根據上文詳述之實施態樣的較佳化合物的實例為以下表中所示之化合物：
Figure 02_image307
Figure 02_image309
Figure 02_image311
Figure 02_image313
Figure 02_image315
Figure 02_image317
Figure 02_image319
Figure 02_image321
Figure 02_image323
Figure 02_image325
Figure 02_image327
Figure 02_image329
Figure 02_image331
Figure 02_image333
Figure 02_image335
Figure 02_image337
Figure 02_image339
Figure 02_image341
本發明化合物之較佳的實施態樣係於實施例中詳細敘述，該等化合物係出於本發明之所有目的而單獨或與其他化合物組合使用。 倘若符合請求項1中所指定的條件，則前述較佳的實施態樣可依需要彼此組合。在本發明之特佳的實施態樣中，前述較佳的實施態樣同時適用。 本發明化合物原則上係以各種方法製備。然而，已發現下文所述之方法特別適合。 因此，本發明進一步提供用於製備本發明化合物之方法，其中合成具有W a基團中至少一者或W a基團中之一者的前驅物之基礎骨架且接著藉助於親核性芳族取代反應或偶合反應引入芳族或雜芳族基團。 包含具有W a基團之基礎骨架之適合的化合物在許多情況下於市場上取得，且在實施例中詳述之起始化合物係以已知的方法獲得，且得以據此參考。 該等化合物可以已知的偶合反應與其他化合物反應，出於此目的之必要條件為熟習本技術領域者已知且在實施例中之詳述規格給予熟習本技術領域者進行該等反應的支援。 所有導致C-C鍵形成及/或C-N鍵形成之特別適合且較佳的偶合反應為那些根據布赫瓦爾德(BUCHWALD)、鈴木(SUZUKI)、山本(YAMAMOTO)、史帝勒(STILLE)、赫克(HECK)、根岸(NEGISHI)、薗頭(SONOGASHIRA)和檜山(HIYAMA)之反應。該等反應已廣為人知，且實施例將提供熟習本技術領域者更多的提示。 上文詳述之製備方法的原理原則上係自用於類似化合物之文獻已知，且可由熟習本技術領域者輕易地調整以製備本發明化合物。更多的訊息可見於實施例中。 以該等方法(若必要時隨後純化，例如再結晶或昇華)有可能獲得高純度的本發明化合物，較佳為大於99%(藉助於 1H NMR及/或HPLC測定)。 本發明化合物亦可與聚合物混合。同樣有可能將該等化合物共價併入聚合物中。這以經反應性脫離基(諸如溴、碘、氯、硼酸或硼酸酯)或經反應性可聚合基團(諸如烯烴或氧呾)取代之化合物尤其有可能。可發現該等用作為製造對應的寡聚物、樹枝狀聚合物或聚合物之單體的用途。寡聚合反應或聚合反應較佳地經由鹵素官能性或硼酸官能性或經由可聚合基團來實現。另外有可能使聚合物經由此類型的基團交聯。本發明化合物及聚合物可以交聯或未交聯層的形式使用。 本發明因此進一步提供含有上文詳述的式(I)及此式之較佳的實施態樣之結構或本發明化合物中之一或多者的寡聚物、聚合物或樹枝狀聚合物，其中本發明化合物或式(I)及此式之較佳的實施態樣之結構有一或多個連接至聚合物、寡聚物或樹枝狀聚合物的鍵存在。根據式(I)及此式之較佳的實施態樣之結構或化合物的鍵聯，該等因此形成寡聚物或聚合物之側鏈或鍵結在主鏈內。聚合物、寡聚物或樹枝狀聚合物可共軛、部分共軛或非共軛。寡聚物或聚合物可為直鏈、支鏈或樹枝狀。關於寡聚物、樹枝狀聚合物及聚合物中的本發明化合物之重複單元，適用如上述相同的優先選擇。 將用於製備寡聚物或聚合物的本發明之單體均聚合或與其他單體共聚合。優先選擇為其中式(I)或上文和下文所敘述之較佳的實施態樣之單元係以0.01至99.9 mol%，較佳為5至90 mol%，更佳為20至80 mol%之程度存在的共聚物。形成聚合物基礎骨架之適合且較佳的共單體係選自茀(例如根據EP 842208或WO 2000/022026)、螺二茀(例如根據EP 707020、EP 894107或WO 2006/061181)、對伸苯基(例如根據WO 92/18552)、咔唑(例如根據WO 2004/070772或WO 2004/113468)、噻吩(例如根據EP 1028136)、二氫菲(例如根據WO 2005/014689)、順-和反-茚并茀(例如根據WO 2004/041901或WO 2004/113412)、酮(例如根據 WO 2005/040302)、菲(例如根據WO 2005/104264或 WO 2007/017066)或其他複數個該等單元。聚合物、寡聚物及樹枝狀聚合物仍可含有其他單元，例如電洞傳輸單元(尤其為那些基於三芳基胺之單元)及/或電子傳輸單元。 另外特別關注以高玻璃轉移溫度為特性之本發明化合物。就此點而言，尤其優先選擇為包含式(I)或上文和下文所敘述之較佳的實施態樣之結構的本發明化合物，其具有依照DIN 51005(2005-08版本)所測定之至少70℃，更佳為至少110℃，甚至更佳為至少125℃，且尤佳為至少150℃之玻璃轉移溫度。 本發明化合物之調配物為自液相加工本發明化合物(例如藉由旋轉塗佈法或藉由印刷法)所必要的。該等調配物可為例如溶液、分散液或乳液。出於此目的，可能較佳的是使用二或更多種溶劑之混合物。適合且較佳的溶劑為例如甲苯、苯甲醚、鄰-、間-或對-二甲苯、苯甲酸甲酯、均三甲苯、四氫萘、藜蘆醚、THF、甲基-THF、THP、氯苯、二㗁烷、苯氧基甲苯(尤其為3-苯氧基甲苯)、(-)-葑酮、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲萘、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯啶酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、α-萜品醇、苯并噻唑、苯甲酸丁酯、異丙苯、環己醇、環己酮、環己基苯、十氫萘、十二烷基苯、苯甲酸乙酯、二氫化茚、NMP、對-異丙基甲苯、苯乙醚(phenetole)、1,4-二異丙基苯、二苯甲醚、二乙二醇丁基甲醚、三乙二醇丁基甲醚、二乙二醇二丁醚、三乙二醇二甲醚、二乙二醇單丁醚、三丙二醇二甲醚、四乙二醇二甲醚、2-異丙萘、戊基苯、己基苯、庚基苯、辛基苯、1,1-雙(3,4-二甲基苯基)乙烷、2-甲基聯苯、3-甲基聯苯、1-甲基萘、1-乙基萘、辛酸乙酯、癸二酸二乙酯、辛酸辛酯、庚基苯、異戊酸薄荷醇酯(menthyl isovalerate)、己酸環己酯或該等溶劑之混合物。 本發明因此本進一步提供包含至少一種本發明化合物及至少一種其他化合物之調配物或組成物。其他化合物可為例如溶劑，尤其為前述溶劑中之一者或該等溶劑之混合物。若其他化合物包含溶劑，則此混合物在本文稱為調配物。其他化合物可另一選擇為至少一種同樣地用於電子裝置的其他有機或無機化合物，例如發光體及/或基質材料，其中該等化合物不同於本發明化合物。適合的發光體及基質材料列在與有機電致發光裝置有關的後文。其他化合物亦可為聚合物。 本發明因此又進一步提供包含至少一種式(I)化合物
Figure 02_image343
其中所使用之符號具有上文給出之定義，較佳為至少一種本發明化合物或包含式(I)之結構的寡聚物、聚合物或樹枝狀聚合物，及至少一種其他的有機功能性材料之組成物。功能性材料通常為引入陽極與陰極之間的有機或無機材料。有機功能性材料較佳地選自由下列所組成之群組：螢光發光體、磷光發光體、展現TADF (熱活化延遲螢光)之發光體、主體材料、電子傳輸材料、電子注入材料、電洞傳導材料、電洞注入材料、電子阻擋材料、電洞阻擋材料、寬能帶隙材料和n-摻雜劑。 本發明進一步提供式(I)化合物
Figure 02_image345
其中所使用之符號具有上文給出之定義，較佳為本發明化合物或包含式(I)之結構的寡聚物、聚合物或樹枝狀聚合物於電子裝置，尤其於有機電致發光裝置之用途，較佳地作為發光體，更佳地作為綠色、紅色或藍色發光體。在此例子中，本發明化合物較佳地展現螢光性質且因此優先提供螢光發光體。 較佳地可能為以下例子：使用式(II-2)至(II-8)、(II-17)至(II-23)、(III-2)至(III-8)、(III-17)至(III-23)、(IV-2)至(IV-8)、(IV-17)至(IV-23)、(V-1)、(V-2)、(V-5)及/或(V-6)之結構/化合物作為發光體。 另外，可使用式(I)化合物或包含式(I)之結構的寡聚物、聚合物或樹枝狀聚合物作為主體材料及/或電子傳輸材料。較佳地可能為以下例子：使用具有蒽基團(Ar-76)至(Ar-78)，較佳為(Ar-78)之結構/化合物、及/或式(II-9)、(II-10)、(II-24)、(II-25)、(III-9)、(III-10)、(III-24)、(III-25)、(IV-9)、(IV-10)、(IV-24)及/或(IV-25)化合物作為電子傳輸材料及/或基質材料。 本發明又進一步提供包含至少一種式(I)化合物
Figure 02_image347
其中所使用之符號具有上文給出之定義，較佳為本發明化合物或包含式(I)之結構的寡聚物、聚合物或樹枝狀聚合物之電子裝置。在本發明之上下文中的電子裝置為包含至少一層包含至少一種有機化合物之裝置。此組件亦可包含無機材料或完全自無機材料所形成的其他層。 電子裝置更佳地選自由下列所組成之群組：有機電致發光裝置(OLED、sOLED、PLED、LEC等)，較佳為有機發光二極體(OLED)、以小分子為主的有機發光二極體(sOLED)、以聚合物為主的有機發光二極體(PLED)、發光電化學電池(LEC)、有機雷射二極體(O-雷射)、有機電漿子發光裝置(D. M. Koller等人之 Nature Photonics2008, 1-4)、有機積體電路(O-IC)、有機場效電晶體(O-FET)、有機薄膜電晶體(O-TFT)、有機發光電晶體(O-LET)、有機太陽能電池(O-SC)、有機光學檢測器、有機感光器、有機場淬滅裝置(O-FQD)和有機電感測器，較佳為有機電致發光裝置(OLED、sOLED、PLED、LEC等)，更佳為有機發光二極體(OLED)、以小分子為主的有機發光二極體(sOLED)、以聚合物為主的有機發光二極體(PLED)，尤其為磷光OLED。 有機電致發光裝置包含陰極、陽極及至少一個發光層。除了該等層以外，其亦可包含其他層，例如在各例子中的一或多個電洞注入層、電洞傳輸層、電洞阻擋層、電子傳輸層、電子注入層、激子阻擋層、電子阻擋層及/或電荷產生層。同樣有可能例如在兩個發光層之間引入具有激子阻擋功能之中間層。然而，應指出每一該等層不一定都必須存在。在此例子中，有機電致發光裝置有可能含有一發光層或含有複數個發光層。若有複數個發光層存在，則該等層較佳地具有多個總計介於380 nm與750 nm之間的最大發射值，使得整體生成白色發光；換言之，將可發螢光或發磷光的各種發光化合物用於發光層中。尤佳的是具有三個發光層之系統，其中三個層顯示藍色、綠色及橘色或紅色發光。本發明之有機電致發光裝置亦可為串聯的電致發光裝置，尤其為白色發光OLED。 本發明化合物可根據精確結構而用於不同的層中。優先選擇為包含在發光層中作為發光體，較佳地作為紅色、綠色或藍色發光體的式(I)或上文詳述之較佳的實施態樣之結構/化合物的有機電致發光裝置。非常佳的是包含在發光層中作為藍色螢光發光體的式(I)或上文詳述之較佳的實施態樣之結構/化合物的有機電致發光裝置。在此尤其優先選擇為式(II-2)至(II-8)、(II-17)至(II-23)、(III-2)至(III-8)、(III-17)至(III-23)、(IV-2)至(IV-8)、(IV-17)至(IV-23)、(V-1)、(V-2)、(V-5)及/或(V-6)之結構/化合物。 當本發明化合物用作為發光層中的發光體時，優先選擇使用本身已知為適合的基質材料(亦稱為主體材料)。 本發明化合物與基質材料之較佳的混合物含有以發光體與基質材料之總體混合物為基礎介於99體積%與1體積%之間，較佳為介於98體積%與10體積%之間，更佳為介於97體積%與60體積%之間，且尤其為介於95體積%與80體積%之間的基質材料。混合物對應地含有以發光體與基質材料之總體混合物為基礎介於1體積%與99體積%之間，較佳為介於2體積%與90體積%之間，更佳為介於3體積%與40體積%之間，且尤其為介於5體積%與20體積%之間的發光體。 可與本發明化合物組合使用之適合的基質材料為芳族酮、芳族膦氧化物或芳族亞碸或碸(例如根據 WO 2004/013080、WO 2004/093207、WO 2006/005627或WO 2010/006680)、三芳基胺、咔唑衍生物(例如CBP (N,N-雙咔唑基聯苯)或在WO 2005/039246、 US 2005/0069729、JP 2004/288381、EP 1205527、 WO 2008/086851或WO 2013/041176中所揭示之咔唑衍生物)、吲哚并咔唑衍生物(例如根據WO 2007/063754或 WO 2008/056746)、茚并咔唑衍生物(例如根據 WO 2010/136109、WO 2011/000455、WO 2013/041176或WO 2013/056776)、氮雜咔唑衍生物(例如根據 EP 1617710、EP 1617711、EP 1731584、JP 2005/347160) 、雙極性基質材料(例如根據WO 2007/137725)、矽烷(例如根據WO 2005/111172)、氮雜硼呃(azaborole)或硼酸酯(例如根據WO 2006/117052)、三𠯤衍生物(例如根據 WO 2007/063754、WO 2008/056746、WO 2010/015306、WO 2011/057706、WO 2011/060859或WO 2011/060877)、鋅錯合物(例如根據EP 652273或WO 2009/062578)、二氮雜矽呃(diazasilole)或四氮雜矽呃(tetraazasilole)衍生物(例如根據WO 2010/054729)、二氮雜磷呃(diazaphosphole)衍生物(例如根據WO 2010/054730)、橋連咔唑衍生物(例如根據WO 2011/042107、WO 2011/060867、WO 2011/088877和WO 2012/143080)、聯伸三苯衍生物(例如根據 WO 2012/048781)、二苯并呋喃衍生物(例如根據 WO 2015/169412、WO 2016/015810、WO 2016/023608、WO 2017/148564或WO 2017/148565)或雙咔唑(例如根據 JP 3139321 B2)。 另外，所使用之共主體可為若參與但不以顯著程度參與電荷傳輸之化合物，如例如WO 2010/108579中所述。尤其適合與本發明化合物組合作為共基質材料的是具有大能帶隙且本身若有任何參與但至少不以顯著程度參與發光層之電荷傳輸的化合物。此等材料較佳為純烴。此等材料的實例可見於例如WO 2009/124627或WO 2010/006680中。 在較佳的組態中，用作為發光體之含有式(I)或上文詳述之較佳的實施態樣之結構/化合物的化合物較佳地與一或多種磷光材料(三重態發光體)及/或為TADF (熱活化延遲螢光)主體材料之化合物組合使用。在此優先選擇形成如WO 2012/133188中所述之超螢光系統及/或如2017271611之超磷光系統。此組合為根據本發明之較佳的組成物。 WO 2015/091716 A1和WO 2016/193243 A1 揭示含有磷光化合物及螢光發光體兩者於發光層中的OLED，其中能量係自磷光化合物轉移至螢光發光體(超磷光)。在此上下文中，磷光化合物因此能作為主體材料起作用。如熟習本技術領域者已知，主體材料具有比發光體更高的單重態及三重態能量，以便使來自主體材料的能量亦以最大效率轉移至發光體。以先前技術所揭示之系統確實具有此能量關係。 應理解在本發明之上下文中的磷光意指來自具有較高的自旋多重性(亦即自旋態＞1)之激發態的發光，尤其為來自激發三重態的發光。在本申請案之上下文中，具有過渡金屬或鑭系元素之所有發光錯合物，尤其為所有的銥、鉑和銅錯合物應視為磷光化合物。 適合的磷光化合物(=三重態發光體)尤其為在適當地激發時發射較佳地在可見光區域內的光且亦含有至少一種原子序大於20，較佳為大於38及小於84，更佳為大於56及小於80的原子(尤其為具有此原子序之金屬)之化合物。所使用之較佳的磷光發光體為含有銅、鉬、鎢、錸、釕、鋨、銠、銥、鈀、鉑、銀、金或銪之化合物，尤其為含有銥或鉑之化合物。 上文所述之發光體的實例可見於申請案WO 00/70655 、WO 2001/41512、WO 2002/02714、WO 2002/15645、 EP 1191613、EP 1191612、EP 1191614、WO 05/033244、WO 05/019373、US 2005/0258742、WO 2009/146770、 WO 2010/015307、WO 2010/031485、WO 2010/054731、WO 2010/054728、WO 2010/086089、WO 2010/099852、WO 2010/102709、WO 2011/032626、WO 2011/066898、WO 2011/157339、WO 2012/007086、WO 2014/008982、WO 2014/023377、WO 2014/094961、WO 2014/094960、WO 2015/036074、WO 2015/104045、WO 2015/117718、WO 2016/015815、WO 2016/124304、WO 2017/032439、WO 2018/011186、WO 2018/001990、WO 2018/019687、WO 2018/019688、WO 2018/041769、WO 2018/054798、WO 2018/069196、WO 2018/069197、WO 2018/069273、WO 2018/178001、WO 2018/177981、WO 2019/020538、WO 2019/115423、WO 2019/158453和WO 2019/179909中。通常如根據先前技術用於磷光電致發光裝置及如那些熟習有機電致發光裝置之技術領域者已知的所有磷光錯合物皆適合，且熟習本技術領域者能夠不運用創新的技能而使用其他的磷光錯合物。 本發明化合物較佳地可與如上文闡述之TADF主體材料及/或TADF發光體組合使用。 稱為熱活化延遲螢光(TADF)之方法係由例如B. H. Uoyama等人之Nature 2012, Vol. 492, 234說明。為了能進行此方法，在發光體中需要例如小於約2000 cm -1之較小的單重態-三重態分離ΔE(S 1-T 1)。為了開啟原則上自旋禁止之
Figure 02_image349
躍遷，除了發光體以外，有可能在具有強的自旋軌道耦合之基質中提供其他化合物，使得經由空間鄰近性及在分子之間因此有可能的相互作用而能夠系統間轉換，或藉助於發光體中存在的金屬原子而產生自旋軌道耦合。 有關超螢光系統之其他有價值的訊息之來源包括WO2012/133188(Idemitsu)、WO2015/022974(Kyushu Univ. )、WO2015/098975 (Idemitsu)、WO2020/053150 (Merck)和DE202019005189 (Merck)。 有關超磷光系統之其他有價值的訊息之來源包括WO2015/091716 A1、WO2016/193243 A1 (BASF)、 WO01/08230 A1 (Princeton Univ. (Mark Thompson))、US2005/0214575A1 (Fuji)、WO2012/079673 (Merck)、WO2020/053314 (Merck)和WO2020/053315 (Merck)。 在本發明進一步的實施態樣中，本發明之有機電致發光裝置不含有任何單獨的電洞注入層及/或電洞傳輸層及/或電洞阻擋層及/或電子傳輸層，此意指發光層直接鄰接電洞注入層或陽極，及/或發射層直接鄰接電子傳輸層或電子注入層或陰極，如例如WO 2005/053051中所述。另外有可能使用與發光層中的金屬錯合物相同或類似的金屬錯合物作為直接鄰接發光層之電洞傳輸或電洞注入材料，如例如WO 2009/030981中所述。 亦較佳的是包含式(I)或上文詳述之較佳的實施態樣之結構/化合物作為電子傳導層中的電子傳輸材料之有機電致發光裝置。在此尤其優先選擇為具有蒽基團，較佳為式(Ar-76)至(Ar-78)，較佳為(Ar-78)之基團的化合物、及/或式(II-9)、(II-10)、(II-24)、(II-25)、(III-9)、(III-10)、(III-24)、(III-25)、(IV-9)、(IV-10)、(IV-24)及/或(IV-25)之結構/化合物。 在本發明之有機電致發光裝置的其他層中，有可能使用如通常根據先前技術所使用之任何材料。熟習本技術領域者因此能夠不運用創新的技能而使用已知用於有機電致發光裝置之任何材料與式(I)或上文敘述之較佳的實施態樣之結構/化合物組合。 另外較佳的是以一或多層係以昇華方法塗佈為特徵之有機電致發光裝置。在此例子中，材料係在真空昇華系統中以低於10 -5毫巴，較佳為低於10 -6毫巴之初始壓力下經氣相沉積法施加。然而，亦有可能以甚至更低的初始壓力，例如低於10 -7毫巴。 同樣地，優先選擇為以一或多層係以OVPD (有機氣相沉積)方法或輔以載體氣體昇華法塗佈為特徵之有機電致發光裝置。在此例子中，材料係在介於10 -5毫巴與1巴之間的壓力下施加。此方法的特殊例子為OVJP(有機蒸氣噴射印刷)方法，其中材料係以噴嘴直接施加且因此結構化。 另外，優先選擇為以一或多層係自溶液製造為特徵之有機電致發光裝置，例如藉由旋轉塗佈或藉由任何印刷方法，例如網版印刷、快乾印刷、平版印刷、LITI(光誘致熱成像、熱轉移印刷)、噴墨印刷或噴嘴印刷。可溶性化合物為此目的所必要的，其係例如通過適合的取代而獲得。 應用式(I)或上文詳述之其較佳的實施態樣之化合物的調配物為新穎的。本發明因此進一步提供含有至少一種溶劑及根據式(I)或上文詳述之其較佳的實施態樣之化合物的調配物。 另外，有可能以混成方法，其中例如一或多層係自溶液施加及一或多個其他層係以氣相沉積法施加。 那些熟習本技術領域者通常知道該等方法且能夠不運用創新的技能而應用該等方法至包含本發明化合物之有機電致發光裝置。 本發明化合物及本發明之有機電致發光裝置具有超越先前技術的壽命改進之特別的特性。同時，電致發光裝置之其他電子性質(諸如效率或操作電壓)維持至少一樣良好。在另一變型中，與先前技術相比，本發明化合物及本發明之有機電致發光裝置尤其以改進的效率及/或操作電壓及更高的壽命為特性。 本發明之電子裝置，尤其為有機電致發光裝置係以下列超越先前技術的驚人優點中之一或多者而值得注意： 1.   包含式(I)或已於上文及下文敘述之較佳的實施態樣之結構/化合物(作為發光體)的電子裝置，尤其為有機電致發光裝置具有非常窄的發光帶，其具有非常低的FWHM(全寬半高)值，且導致特別純的色發光，其以低的CIE y值可識別。在此特別驚人的是提供具有低的FWHM值之藍色發光體及發射光在色譜的綠色、黃色或紅色區域之具有低的FWHM值之發光體兩者。 2.   包含式(I)或已於上文及下文敘述之較佳的實施態樣之結構/化合物(尤其作為發光體，作為電洞傳導材料及/或作為電子傳輸材料)的電子裝置，尤其為有機電致發光裝置具有非常良好的壽命。在此上下文中，該等化合物尤其造成低衰減(roll-off)，亦即裝置在高發光強度下具有小的功率效率下降。 3.   包含式(I)或已於上文及下文敘述之較佳的實施態樣之結構/化合物(作為發光體及/或作為電子傳輸材料)的電子裝置，尤其為有機電致發光裝置具有極佳的效率。在此上下文中，當本發明之式(I)或以上文及下文所敘述之較佳的實施態樣之結構/化合物用於電子裝置時，其造成低的操作電壓。 4.   本發明之式(I)或以上文及下文所敘述之較佳的實施態樣之結構/化合物展現非常高的穩定性及壽命。 5.   以式(I)或以上文及下文所敘述之較佳的實施態樣之結構/化合物有可能避免在電子裝置，尤其在有機電致發光裝置中形成光損耗通道。因此，該等裝置係以發光體的高PL效率和因此高EL效率，及基質對摻雜物之極佳的能量傳輸為特性。 激子能量通常係經由所謂的戴克斯特轉移(Dexter transfer)或經由福斯特轉移(Förster transfer)而自發光層中的基質或主體傳輸至發光體。在此以自主體或基質至本發明之發光體的福斯特能量轉移(FRET)特佳，因為其特別有效，其導致電子裝置具有特別良好的性能數據(例如效率、電壓和壽命)。發現能量較佳地經由福斯特轉移而自主體或基質轉移至本發明化合物。 6.   式(I)或以上文及下文所敘述之較佳的實施態之結構/化合物具有極佳的玻璃成膜性。 7.   式(I)或以上文及下文所敘述之較佳的實施態之結構/化合物係自溶液形成非常良好的膜且顯示極佳的溶解性。 該等前述優點未伴隨著其他電子性質之過分高度劣化。 應指出以本發明所述之實施態樣的變化係由本發明之範圍所涵蓋。以本發明所揭示之任何特性可與適合於相同目的或等效或類似目的之替代特性交換，除非經明確地排除。因此，以本發明所揭示之任何特性應被認為是通用系列的實例或等效或類似的特性，除非另有其他聲明。 本發明之所有特性可以任何方式彼此組合，除非特定的特性及/或步驟相互排斥。這對本發明之較佳的特性尤其如此。同樣地，非必要之組合的特性可單獨(且不組合)使用。 亦應指出許多特性及尤其為本發明之較佳的實施態樣的那些特性本身應被視為創新的且不僅僅被視為本發明之一些實施態樣。該等特性除了或作為任何當前請求之發明的替代以外，可對其尋求獨立的保護。 可將本發明所揭示之技術指導列出摘要且與其他實例組合。 本發明係以隨後的實施例更詳細地例證，而沒有任何由此限制本發明之意圖。熟習本技術領域者能夠使用所給出之訊息執行所揭示之整個範圍內的發明，且不運用創新的技能製備本發明之其他化合物，及使用該等化合物於電子裝置中或利用本發明之方法。 The present invention provides a compound comprising at least one structure of formula (I), preferably a compound of formula (I),
Figure 02_image003
wherein the rings Ar are in each case identical or different and are aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms which may be substituted by one or more Ar or R groups, ring Ar b are in each case the same or different and are aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms which may be substituted by one or more Ar or R groups; and wherein Other symbols and labels used are as follows: W a , W b are the same or different in each case and are O or S, preferably O; Ar are the same or different in each case and have 5 An aromatic or heteroaromatic ring system of up to 60 aromatic ring atoms which may be substituted by one or more R groups; the Ar group may be combined with at least one Ar, R, R a , R b group or another The group forms a ring system; R, R a , R b are in each case the same or different and are H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar′) 2 , N(R 1 ) 2 , C(=O)N(Ar') 2 , C(=O)N(R 1 ) 2 , C(Ar') 3 , C(R 1 ) 3 , Si(Ar') 3. Si(R 1 ) 3 , B(Ar') 2 , B(R 1 ) 2 , C(=O)Ar', C(=O)R 1 , P(=O)(Ar') 2 , P(=O)(R 1 ) 2 , P(Ar') 2 , P(R 1 ) 2 , S(=O)Ar', S(=O)R 1 , S(=O) 2 Ar', S(=O) 2 R 1 , OSO 2 Ar', OSO 2 R 1 , linear alkyl, alkoxy or thioalkoxy having 1 to 40 carbon atoms or alkenes having 2 to 40 carbon atoms or alkynyl, or branched or cyclic alkyl, alkoxy or thioalkoxy having 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkyne may be substituted in each instance by one or more R 1 groups, wherein one or more non-adjacent CH 2 groups may be substituted by R 1 C=CR 1 , C≡C, Si(R 1 ) 2 , C=O, C=S, C=Se, C=NR 1 , -C(=O)O-, -C(=O)NR 1 -, NR 1 , P(=O)(R 1 ), - O-, -S-, SO or SO replacement , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may in each case be substituted by one or more R groups, or An aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms which may be substituted by one or more R groups , or having 5 to 60 aromatic ring atoms which may be substituted by one or more R groups A heteroarylthio group substituted by a group, or a diarylamino group, an arylheteroarylamine group, a diheteroarylamino group, which has 5 to 60 aromatic ring atoms and may be substituted by one or more R groups, Or an aralkyl or heteroarylalkyl group having 5 to 60 aromatic ring atoms and 1 to 10 carbon atoms in the alkyl group may be substituted by one or more R groups; meanwhile, two R, The R a , R b groups can also form a ring system together or with another group; Ar' are in each case the same or different and have 5 to 60 aromatic ring atoms and can be replaced by one or more Aromatic or heteroaromatic ring system substituted by R1 group; at the same time, two Ar' groups bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom may also be connected via a single bond bridge or a bridge selected from the following: B(R 1 ), C(R 1 ) 2 , Si(R 1 ) 2 , C=O, C=NR 1 , C=C(R 1 ) 2 , O , S, S=O, SO 2 , N(R 1 ), P(R 1 ) and P(=O)R 1 ; R 1 are in each case the same or different and are H, D, F, Cl, Br, I, CN, NO 2 , N(Ar") 2 , N(R 2 ) 2 , C(=O)Ar", C(=O)R 2 , P(=O)(Ar") 2 , P(Ar") 2 , B(Ar") 2 , B(R 2 ) 2 , C(Ar") 3 , C(R 2 ) 3 , Si(Ar") 3 , Si(R 2 ) 3 , straight-chain alkyl, alkoxy or thioalkoxy having 1 to 40 carbon atoms or branched or cyclic alkyl, alkoxy or thioalkoxy having 3 to 40 carbon atoms or having 2 Alkenyl groups of up to 40 carbon atoms, each of which may be substituted by one or more R 2 groups, wherein one or more non-adjacent CH 2 groups may be substituted by -R 2 C=CR 2 - , -C≡C-, Si(R 2 ) 2 , C=O, C=S, C=Se, C=NR 2 , -C(=O)O-, -C(=O)NR 2 -, NR 2 , P(=O)(R 2 ), -O-, -S-, SO or SO 2 and one or more hydrogen atoms can be replaced by D, F, Cl, Br, I, CN or NO 2 Substitution, or aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R groups, or having 5 to 60 aromatic ring atoms and may be substituted by one or more R groups, or aryloxy or heteroaryloxy groups, or arylalkyl or heteroaryl groups having 5 to 60 aromatic ring atoms and may be substituted by one or more R groups Aralkyl, or a combination of these systems; at the same time, two or more preferably adjacent R 1 groups can form a ring system together; at the same time, one or more R 1 groups can be combined with other parts of the compound form a ring system; Ar" is in each case the same or different and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms which may be substituted by one or more R groups; while , two Ar'' groups bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom may also be bonded together via a single bond bridge or a bridge selected from the following: B(R 2 ), C(R 2 ) 2 , Si(R 2 ) 2 , C=O, C=NR 2 , C=C(R 2 ) 2 , O, S, S=O, SO 2 , N(R 2 ) , P(R 2 ) and P(=O)R 2 ; R 2 are in each case the same or different and are selected from the group consisting of: H, D, F, CN, with 1 to 20 Aliphatic hydrocarbon radicals of carbon atoms, or aromatic or heteroaromatic ring systems having 5 to 30 aromatic ring atoms, in which one or more hydrogen atoms may be replaced by D, F, Cl, Br, I or CN, And it can be substituted by one or more alkyl groups each having 1 to 4 carbon atoms; meanwhile, two or more preferably adjacent substituents R 2 can form a ring system together; excluding formula (A), Protection of compounds (B) and (C)
Figure 02_image005
. Protection of compounds of formulas (A), (B) and (C) is excluded. Compound (A) with CAS No. 125213-40-3, compound (B) with CAS No. 131847-09-1 and compound (C) with CAS No. 166042-85-9 are known from prior art , but it is not used in electronic devices. Aryl in the context of the present invention contains 6 to 40 carbon atoms; heteroaryl in the context of the present invention contains 2 to 40 carbon atoms and at least one heteroatom, the prerequisite being the total number of carbon atoms and heteroatoms Mesh is at least 5. Heteroatoms are preferably selected from N, O and/or S. It is understood that aryl or heteroaryl here means a simple aromatic ring, i.e. benzene, or a simple heteroaromatic ring, such as pyridine, pyrimidine or thiophene, etc., or a fused (condensed) aryl or heteroaryl group, such as Naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc. In contrast, aromatic systems joined to each other by a single bond, such as biphenyl, are not referred to as aryl or heteroaryl, but are referred to as aromatic ring systems. Electron-deficient heteroaryl in the context of the present invention is a heteroaryl having at least one heteroaromatic six-membered ring having at least one nitrogen atom. Further aromatic or heteroaromatic five- or six-membered rings may be fused to this six-membered ring. Examples of electron-deficient heteroaryl groups are pyridine, pyrimidine, pyridine, pyrimidine, trisulfone, quinoline, quinazoline or quinoline. Aromatic ring systems in the context of the present invention contain 6 to 60 carbon atoms in the ring system. Heteroaromatic ring systems in the context of the present invention contain 2 to 60 carbon atoms and at least one heteroatom in the ring system, with the proviso that the total number of carbon atoms and heteroatoms is at least 5. Heteroatoms are preferably selected from N, O and/or S. It is understood that an aromatic or heteroaromatic ring system in the context of the present invention means a system not necessarily containing only aryl or heteroaryl groups, but in which two or more aryl or heteroaryl groups are also possible in the form of non- Aromatic units such as carbon, nitrogen or oxygen atoms are joined. For example, systems such as stilbene, 9,9'-spirobistilbene, 9,9-diarylstilbene, triarylamine, diaryl ether, stilbene, etc. are also considered aromatic ring systems in the context of the present invention , and likewise a system in which two or more aryl groups are joined eg by a lower alkyl group. The aromatic ring system is preferably selected from fluorine, 9,9'-spirobistines, 9,9-diarylamines or those in which two or more aryl and/or heteroaryl groups are joined to each other by a single bond. group. In the context of the present invention, it is preferably understood that aliphatic hydrocarbon radicals or alkyl or alkenyl or alkyne groups which may contain from 1 to 20 carbon atoms and in which individual hydrogen atoms or CH2 groups may also be substituted by the aforementioned groups Base means methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secondary butyl, tertiary butyl, 2-methylbutyl, n-pentyl, secondary pentyl , neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-Trifluoroethyl, vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octene Cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. It is preferably understood that alkoxy having 1 to 40 carbon atoms means methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy , secondary butoxy, tertiary butoxy, n-pentyloxy, secondary pentyloxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy , n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy. It is understood that thioalkyl having 1 to 40 carbon atoms especially means methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, secondary butylthio Base, tertiary butylthio, n-pentylthio, secondary pentylthio, n-hexylthio, cyclohexylthio, n-heptylthio, cycloheptylthio, n-octylthio, cyclooctylthio, 2- Ethylhexylthio, Trifluoromethylthio, Pentafluoroethylthio, 2,2,2-Trifluoroethylthio, Vinylthio, Propylthio, Butenylthio, Pentenylthio, Cyclopentylthio Enylthio, Hexenylthio, Cyclohexenylthio, Heptenylthio, Cycloheptenylthio, Octenylthio, Cyclooctenylthio, Ethynylthio, Proynylthio, Butynylthio , pentynylthio, hexynylthio, heptynylthio or octynylthio. The alkyl, alkoxy or alkylthio groups according to the present invention can generally be linear, branched or cyclic, wherein one or more non-adjacent CH groups can be replaced by the above groups; in addition, one or Multiple hydrogen atoms may also be replaced by D, F, Cl, Br, I, CN or NO 2 , preferably by F, Cl or CN, more preferably by F or CN, especially preferably by CN. It is to be understood that aromatic or heteroaromatic compounds having 5 to 60 or 5 to 40 aromatic ring atoms, which may also in each case be substituted by the groups mentioned above, and which may be attached to the aromatic or heteroaromatic system via any desired position. Aromatic ring systems mean in particular groups derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, allene fluoranthene, fused tetraphenyl, fused tetraphenyl Pentaphenyl, benzopyrene, biphenyl, biphenylene, terphenyl, triphenylene, fennel, spirodipic, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans -indenoxene, cis- or trans-indenocarbazole, cis- or trans-indolocarbazole, truxene, isotruxene, spirotrisindene, spiroisotrimer Indene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline , isoquinoline, acridine, phenanthidine, benzo-5,6-quinoline, benzo-6,7-quinoline, benzo-7,8-quinoline, phenanthyl thiophene, morphine 㗁𠯤, pyridine Azole, indazole, imidazole, benzimidazole, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazinimidazole, quinoxalinimidazole, 㗁Azole, benzoxazole, benzoxazole, naphthoxazole, anthroxazole, phenanthroxazole, isoxazole, 1,2-thiazole, 1,3- Thiazole, benzothiazole, thiazole, hexaazatriphenylene, benzopyridine, pyrimidine, benzopyrimidine, quinoline, 1,5-diazaanthracene, 2,7-diazapyrene, 2 ,3-Diazapyrene, 1,6-diazapyrene, 1,8-diazapyrene, 4,5-diazapyrene, 4,5,9,10-tetraazapyrene, pyrene , morphine 𠯤, morphine 㗁 𠯤, phenanthium thiophene 𠯤, fluorubin, phenidine, azacarbazole, benzocarboline, phenanthroline, 1,2,3-triazole, 1,2,4- Triazole, benzotriazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1, 2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,3,5-tri-thiadiazole, 1,2 ,4-three 𠯤, 1,2,3-three 𠯤, tetrazole, 1,2,4,5-tetra 𠯤, 1,2,3,4-tetra 𠯤, 1,2,3,5-tetra 𠯤 , purine, pteridine, indene, and benzothiadiazole, or groups derived from combinations of these systems. In the context of the present description, it is understood that the phrase that two or more groups may together form a ring means in particular that two groups are joined to each other by a chemical bond with the formal elimination of two hydrogen atoms. This is exemplified by the following diagram:
Figure 02_image007
. However, it is additionally understood that the above phrase means that if one of the two groups is hydrogen, the second group is bonded to the hydrogen atom to form a ring. This will be illustrated by the following diagram:
Figure 02_image009
. In a preferred configuration, the compounds of the present invention may comprise structures of formulas (II-1) to (II-42); the compounds of the present invention may be selected from compounds of formulas (II-1) to (II-42) :
Figure 02_image011
Figure 02_image013
Figure 02_image015
Figure 02_image017
Figure 02_image019
Figure 02_image021
Figure 02_image023
Figure 02_image025
Figure 02_image027
Figure 02_image029
Figure 02_image031
Figure 02_image033
Figure 02_image035
Figure 02_image037
Figure 02_image039
Figure 02_image041
Figure 02_image043
Figure 02_image045
Figure 02_image047
Figure 02_image049
Figure 02_image051
Figure 02_image053
Figure 02_image055
Figure 02_image057
Figure 02_image059
Figure 02_image061
Figure 02_image063
Figure 02_image065
Figure 02_image067
Figure 02_image069
Figure 02_image071
Figure 02_image073
Figure 02_image075
Figure 02_image077
Figure 02_image079
Figure 02_image081
Figure 02_image083
Figure 02_image085
Figure 02_image087
Figure 02_image089
Figure 02_image091
Figure 02_image093
where the symbols W a and W b have the definitions given above, especially in formula (I), and the other symbols are as follows: Y a is in each case the same or different and is N(Ar), N(R a ), P(Ar), P(R a ), P(=O)Ar, P(=O)R a , P(=S)Ar, P(=S)R a , B(Ar), B (R a ), Al(Ar), Al(R a ), Ga(Ar), Ga(R a ), C=O, C(R a ) 2 , Si(R a ) 2 , Ge(R a ) 2. C=NR a , C=NAr, C=C(R a ) 2 , C=C(R a )(Ar), O, S, Se, S=O or SO 2 , preferably N(Ar ), N(R a ), B(Ar), B(R a ), P(=O)R a , P(=O)Ar, C=O, C(R a ) 2 , C=C(R a ) 2 , C=C(R a )(Ar), Si(R a ) 2 , O, S, Se, S=O or SO 2 , more preferably N(Ar), C(R a ) 2 , O or S, wherein R a has the definition specified above, especially in formula (I); Y b is in each case the same or different and is N(Ar), N(R b ), P(Ar ), P(R b ), P(=O)Ar, P(=O)R b , P(=S)Ar, P(=S)R b , B(Ar), B(R b ), Al (Ar), Al(R a ), Ga(Ar), Ga(R b ), C=O, C(R b ) 2 , Si(R b ) 2 , Ge(R b ) 2 , C=NR b , C=NAr, C=C(R b ) 2 , C=C(R b )(Ar), O, S, Se, S=O or SO 2 , preferably N(Ar), N(R b ), B(Ar), B(R b ), P(=O)R b , P(=O)Ar, C=O, C(R b ) 2 , C=C(R b ) 2 , C= C(R b )(Ar), Si(R b ) 2 , O, S, Se, S=O or SO 2 , more preferably N(Ar), C(R b ) 2 , O or S, where R b has the definition specified above, especially in formula (I); Y 1 , Y 2 are in each case the same or different and are N(Ar), N(R), P(Ar), P( R), P(=O)Ar, P(=O)R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R) , Ga(Ar), Ga(R), C=O, C(R) 2 , Si(R) 2 , Ge(R) 2 , C=NR, C=NAr, C=C(R) 2 , C =C(R)(Ar), O, S, Se, S=O or SO 2 , preferably N(Ar), N(R), B(Ar), B(R), P(=O) R, P(=O)Ar, C=O, C(R) 2 , C=C(R) 2 , C=C(R)(Ar), Si(R) 2 , O, S, Se, S =O or SO 2 , more preferably N(Ar), C(R) 2 , O or S, wherein R has the definition specified above, especially for formula (I); X is in each case the same or different and is N or CR, preferably CR, with the proviso that not more than two of the X groups in one ring are N, wherein R has the definition specified above, especially in formula (I); X a are the same or different in each case and are N or CR a , preferably CR a , with the proviso that not more than two of the X a groups in one ring are N, where R a has the above, especially Definitions as detailed in formula (I); X b are in each case the same or different and are N or CR b , preferably CR b , with the proviso that there are not more than two X b groups in one ring One is N, wherein R b has the definition detailed above, especially in relation to formula (I). Here, the structures of formulas (II-1) to (II-31) are preferred, and the structures of formulas (II-1) to (II-4), (II-6), (II-8), (II-10), (II-12), (II-14), (II-16) to (II-19), (II-21), (II-23), (II-25), (II -27), (II-29), (II-31) structures. In addition, it is especially preferred to be a compound including the structure of formula (I) and (II-1) to (II-42), at least one of W a and W b groups is O; preferably two W a , The W b groups are all O. If two or more nitrogen atoms are present in the compound, the nitrogen atoms are preferably not adjacent and thus no NN bonds are present. In a further preferred embodiment, the following examples may be: the compound of the present invention includes the structures of formula (III-1) to (III-41), wherein the compound of the present invention can be more preferably selected from the formula (III-1) To (III-41) compound
Figure 02_image095
Figure 02_image097
Figure 02_image099
Figure 02_image101
Figure 02_image103
Figure 02_image105
Figure 02_image107
Figure 02_image109
Figure 02_image111
Figure 02_image113
Figure 02_image115
Figure 02_image117
Figure 02_image119
Figure 02_image121
Figure 02_image123
Figure 02_image125
Figure 02_image127
Figure 02_image129
Figure 02_image131
Figure 02_image133
Figure 02_image135
Figure 02_image137
Figure 02_image139
Figure 02_image141
Figure 02_image143
Figure 02_image145
Figure 02_image147
Figure 02_image149
Figure 02_image151
Figure 02_image153
Figure 02_image155
Figure 02_image157
Figure 02_image159
Figure 02_image161
Figure 02_image163
Figure 02_image165
Figure 02_image167
Figure 02_image169
Figure 02_image171
Figure 02_image173
Figure 02_image175
where the symbols Y 1 , Y 2 , Ya, Y b , X, X a and X b have the meanings given above, especially in formulas ( II-1) to (II-42). Here, the structures of formulas (III-1) to (III-31) are preferred, and the structures of formulas (III-1) to (III-4), (III-6), (III-8), (III-10), (III-12), (III-14), (III-16) to (III-19), (III-21), (III-23), (III-25), (III -27), (III-29), (III-31) structures. The following examples may be preferred: in formulas (II-1) to (II-42) and/or (III-1) to (III-41), no more than four, and preferably no more than two The X, X a and X b groups are N; more preferably all of the X, X a and X b groups are CR, CR a or CR b . In a further preferred embodiment, the following examples may be: the compound of the present invention includes the structures of formula (IV-1) to (IV-41), wherein the compound of the present invention can be more preferably selected from the formula (IV-1) To (IV-41) compound.
Figure 02_image177
Figure 02_image179
Figure 02_image181
Figure 02_image183
Figure 02_image185
Figure 02_image187
Figure 02_image189
Figure 02_image191
Figure 02_image193
Figure 02_image195
Figure 02_image197
Figure 02_image199
Figure 02_image201
Figure 02_image203
Figure 02_image205
Figure 02_image207
Figure 02_image209
Figure 02_image211
Figure 02_image213
Figure 02_image215
Figure 02_image217
Figure 02_image219
Figure 02_image221
Figure 02_image223
Figure 02_image225
Figure 02_image227
Figure 02_image229
Figure 02_image231
Figure 02_image233
Figure 02_image235
Figure 02_image237
Figure 02_image239
Figure 02_image241
Figure 02_image243
Figure 02_image245
Figure 02_image247
Figure 02_image249
Figure 02_image251
Figure 02_image253
Figure 02_image255
Figure 02_image257
wherein the symbols R, R a and R b have the definitions given above, especially in formula (I), and the symbols Y 1 , Y 2 , Ya and Y b have the above, especially in formulas (II-1) to ( II-42), and other symbols have the following definitions: m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2; j is 0, 1 or 2, preferably 0 or 1. Here preference is given to structures/compounds of formulas (IV-1) to (IV-31), and particularly preference is given to structures/compounds of formulas (IV-1) to (IV-4), (IV-6), (IV-8 ), (IV-10), (IV-12), (IV-14), (IV-16) to (IV-19), (IV-21), (IV-23), (IV-25), Structures/compounds of (IV-27), (IV-29), (IV-31). Possible further examples are: the Y a and Y b groups are the same. Additionally, the Y a and Y b groups may be different. In a further configuration, the following examples are possible: one of the Y a and Y b groups is O, and one of the Y a and Y b groups is C(R a ) 2 or C(R b ) 2 . In a further embodiment, the following examples are possible: one of the Y a and Y b groups is Nar, and one of the Y a and Y b groups is C(R a ) 2 or C(R b ) 2 . The following example is also possible: the Y1 and Y2 groups are the same. Additionally, the Y1 and Y2 groups can be different. In a further configuration, the following examples are possible: one of the Y 1 and Y 2 groups is O, and one of the Y 1 and Y 2 groups is C(R a ) 2 or C(R b ) 2 . In a further embodiment, the following examples are possible: one of the Y 1 and Y 2 groups is NAr, and one of the Y 1 and Y 2 groups is C(R a ) 2 or C(R b ) 2 . In a further preferred embodiment, the following examples may be: the compound of the present invention includes the structures of formulas (V-1) to (V-8), wherein the compound of the present invention can be more preferably selected from the formula (V-1) to (V-8) compound
Figure 02_image259
Figure 02_image261
Figure 02_image263
Figure 02_image265
where the symbols R a and R b have the definitions given above, especially in formula (I), and the other symbols have the following definitions: R c , R d are in each case the same or different and are N(Ar' ) 2 , N(R 1 ) 2 , C(=O)N(Ar') 2 , C(=O)N(R 1 ) 2 , C(Ar') 3 , C(R 1 ) 3 , Si( Ar') 3 , Si(R 1 ) 3 , B(Ar') 2 , B(R 1 ) 2 , C(=O)Ar', C(=O)R 1 , P(=O)(Ar' ) 2 , P(=O)(R 1 ) 2 , P(Ar') 2 , P(R 1 ) 2 , S(=O)Ar', S(=O)R 1 , S(=O) 2 Ar', S(=O) 2 R 1 , OSO 2 Ar', OSO 2 R 1 , linear alkyl, alkoxy or thioalkoxy having 1 to 40 carbon atoms or having 2 to 40 carbons atom alkenyl or alkynyl, or branched or cyclic alkyl, alkoxy or thioalkoxy having 3 to 20 carbon atoms, wherein such alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl groups may in each case be substituted by one or more R 1 groups, wherein one or more non-adjacent CH 2 groups may be substituted by R 1 C=CR 1 , C≡C, Si(R 1 ) 2 , C=O, C=S, C=Se, C=NR 1 , -C(=O)O-, -C(=O)NR 1 -, NR 1 , P(=O)(R 1 ), -O-, -S-, SO or SO replacement, or an aromatic or heteroaromatic ring having 5 to 60 aromatic ring atoms and which may in each case be substituted by one or more R groups system, or aryloxy or heteroaryloxy having 5 to 60 aromatic ring atoms and which may be substituted by one or more R groups, or having 5 to 60 aromatic ring atoms and which may be substituted by one or more A heteroarylthio group substituted by R1 groups, or a diarylamino group, an arylheteroarylamino group, a diheteroaryl group having 5 to 60 aromatic ring atoms and which may be substituted by one or more R1 groups Amino group, or an arylalkyl or heteroarylalkyl group having 5 to 60 aromatic ring atoms and 1 to 10 carbon atoms in the alkyl group which may be substituted by one or more R groups; and , one R c group can form a ring system with R, R a , R b , R d group or another group; at the same time, the R d group can form a ring system with R, R a , R b , R c group or Another group forms a ring system; m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2; n is 0, 1, 2 or 3, preferably 0, 1 or 2. In addition, especially with regard to structures/compounds of formulas (V-1) to (V-8), the following examples are possible: R c and R d groups are the same. Additionally, the Rc and Rd groups may be different. The sum of the labels j, m and n (especially in structures/compounds of formulas (IV-1) to (IV-41) and/or (V-1) to (V-8)) is preferably at most 10, more Preferably, it is not more than 8, more preferably, it is not more than 6, and more preferably, it is not more than 4. In addition, including (I), (II-1) to (II-42), (III-1) to (III-42), (IV-1) to (IV-41), (V-1) to In the preferred embodiment of the formula (V-8) and/or the equation described in detail below, it may be the following examples: at least one R, R a , R b , R c , R d group has Straight-chain alkyl, alkoxy or thioalkoxy of 1 to 40 carbon atoms, or alkenyl or alkynyl of 2 to 40 carbon atoms, or branched or cyclic of 3 to 20 carbon atoms Alkyl, alkoxy or thioalkoxy, wherein such alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl may in each instance be substituted by one or more R groups, one of which Or multiple non-adjacent CH 2 groups can be via R 1 C=CR 1 , C≡C, Si(R 1 ) 2 , C=O, C=S, C=Se, C=NR 1 , -C (=O)O-, -C(=O)NR 1 -, NR 1 , P(=O)(R 1 ), -O-, -S-, SO or SO 2 substitutions, or having 5 to 60 Aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms and which may in each case be substituted by one or more R groups or which may be substituted by one or more R 1 group substituted aryl or heteroaryloxy group, or a heteroarylthio group having 5 to 60 aromatic ring atoms which may be substituted by one or more R groups, or a heteroarylthio group having 5 to 60 aromatic ring atoms Aromatic ring atoms and may be substituted by one or more R 1 group diarylamine, aryl heteroarylamine, diheteroarylamine, or have 5 to 60 aromatic ring atoms and in the alkyl An arylalkyl or heteroarylalkyl group of 1 to 10 carbon atoms which may be substituted with one or more R groups . Including (I), (II-1) to (II-42), (III-1) to (III-42), (IV-1) to (IV-41), (V-1) to (V In the preferred implementation of the formula of -8) and/or the equation described in detail below, the following examples may be preferred: at least one R, R a , R b , R c , R d group is Aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms which may in each case be substituted by one or more R groups, or having 5 to 60 aromatic ring atoms which may be substituted by one or a plurality of R 1 groups substituted aryl or heteroaryloxy, or a heteroarylthio group having 5 to 60 aromatic ring atoms which may be substituted by one or more R 1 groups, or a heteroarylthio group having 5 Diarylamine, arylheteroarylamine, diheteroarylamine having up to 60 aromatic ring atoms and which may be substituted by one or more R groups, or having 5 to 60 aromatic ring atoms and An arylalkyl or heteroarylalkyl group of 1 to 10 carbon atoms in the alkyl group which may be substituted by one or more R groups, more preferably has 5 to 60 aromatic ring atoms and may be in In each case an aromatic or heteroaromatic ring system substituted with one or more R1 groups. In a preferred development of the invention, the following examples are possible: at least two R, R a , R b , R c , R d groups and the two R, Ra, R b , R c , R d groups The other groups combined form a fused ring together, wherein two R, R a , R b , R c , R d groups form at least one structure of formulas (RA-1) to (RA-12):
Figure 02_image267
Figure 02_image269
Figure 02_image271
Figure 02_image273
wherein R has the definition detailed above, the dotted bond represents the linking site through which the two R, R a , R b , R c , R d groups are bound to other groups, and the other symbols have the following definitions: Y 3 is in each case the same or different and is C(R 1 ) 2 , (R 1 ) 2 CC(R 1 ) 2 , (R 1 )C=C(R 1 ), NR 1 , NAr′ , O or S, preferably C(R 1 ) 2 , (R 1 ) 2 CC(R 1 ) 2 , (R 1 )C=C(R 1 ), O or S; R e in each case is The same or different and are F, straight-chain alkyl, alkoxy or thioalkoxy having 1 to 40 carbon atoms, or alkenyl or alkynyl having 2 to 40 carbon atoms, or having 3 to 40 carbon atoms 20 carbon atoms branched or cyclic alkyl, alkoxy or thioalkoxy, wherein these alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl can be in each example through one or Multiple R 2 groups are substituted, wherein one or more adjacent CH 2 groups can be replaced by R 2 C=CR 2 , C≡C, Si(R 2 ) 2 , C=O, C=S, C= Se, C=NR 2 , -C(=O)O-, -C(=O)NR 2 -, NR 2 , P(=O)(R 1 ), -O-, -S-, SO or SO 2 substituted, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may in each case be substituted by one or more R groups , or having 5 to 60 aromatic ring atoms and Aryloxy or heteroaryloxy groups which may be substituted by one or more R groups; at the same time, it is also possible to have two R groups together or one R group together with R group or with another The groups together form a ring system; s is 0, 1, 2, 3, 4, 5 or 6, preferably 0, 1, 2, 3 or 4, more preferably 0, 1 or 2; t is 0, 1 , 2, 3, 4, 5, 6, 7 or 8, preferably 0, 1, 2, 3 or 4, more preferably 0, 1 or 2; v is 0, 1, 2, 3, 4, 5 , 6, 7, 8 or 9, preferably 0, 1, 2, 3 or 4, more preferably 0, 1 or 2. In a preferred embodiment of the present invention, at least two R, R a , R b , R c , R d groups are combined with the two R, R a , R b , R c , R d groups The other groups together form a fused ring, wherein two R, R a , R b , R c , R d groups preferably form at least one of the structures of formulas (RA-1a) to (RA-4f) :
Figure 02_image275
Figure 02_image277
Wherein the dotted line bond represents the connection site, through which the two R, R a , R b , R c , R d groups are bound to other groups, and the label m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and the symbols R 1 , R 2 , Re and the symbols s and t have the definitions described above, especially in formula (I) and/or formulas (RA-1) to (RA-12) . Possible further examples are: at least two R, R a , R b , R c , R d groups form formulas (RA-1) to (RA-12) and/or (RA-1a) to (RA-4f ) and form a fused ring, represent the R, Ra, R b , R c , R d groups from adjacent X, X a , X b groups, or represent the groups bonded to adjacent carbon atoms respectively R, R a , R b , R c , R d groups, wherein the carbon atoms are preferably connected via a bond. In a further preferred configuration, at least two R, R a , R b , R c , R d groups are combined with other groups of the two R, R a , R b , R c , R d groups The groups form a fused ring together, wherein two R, R a , R b , R c , R d groups form a structure of formula (RB),
Figure 02_image279
wherein R has the definition set forth above, especially in formula (I), the dotted bond represents the bonding site through which the two R, R a , R b , R c , R d groups are bound to other groups , the label m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2, and Y 4 is C(R 1 ) 2 , NR 1 , NAr', BR 1 , BAr', O or S, Preferably it is C(R 1 ) 2 , NAr' or O. The following examples are possible here: at least two R, R a , R b , R c , R d groups form a structure of formula (RB) and form a condensed ring, representing a group from adjacent X, X a , X b R, R a , R b , R c , R d groups of the group, or R, R a , R b , R c , R d groups respectively bonded to adjacent carbon atoms, wherein the carbon The atoms are preferably connected via bonds. The compound preferably comprises at least one structure of formula (VI-1) to (VI-22); the compound is more preferably selected from the compound of formula (VI-1) to (VI-22), wherein the compound has at least one fused ring :
Figure 02_image281
Figure 02_image283
Figure 02_image285
Wherein the symbols R, R a , R b , Y 1 and Y 2 have the definitions given above, especially in formula (I) and/or formulas (II-1) to (II-42), and the symbol o represents the linking position point, and other symbols have the following definitions: m is 0, 1, 2, 3 or 4, preferably 0, 1 or 2; j is 0, 1 or 2, preferably 0 or 1; k is 0 or 1 . Preference is given here to the structures/compounds of the formulas (VI-1) to (VI-4). The compound preferably comprises at least one structure of formula (VII-1) to (VII-4); the compound is more preferably selected from the compound of formula (VII-1) to (VII-4), wherein the compound has at least one fused ring :
Figure 02_image287
wherein the symbols R, R a and R b have the definitions given above, especially in formula (I), the symbol o represents the attachment point of the fused ring, and the other symbols have the following definitions: j is 0, 1 or 2, Preferably it is 0 or 1; k is 0 or 1. The fused rings (especially in formulas (VI-1) to (VI-22) and/or (VII-1) to (VII-4)) are preferably composed of at least two R, R a , R b , R c , R d groups and other groups combined with the two R, R a , R b , R c , R d groups are formed, wherein at least two R, R a , R b , R c , R d The groups form the structures of formulas (RA-1) to (RA-12) and/or formula (RB), preferably the structures of formulas (RA-1) to (RA-12). The following examples may be preferred: the compound has at least two fused rings, at least one of which is represented by formulas (RA-1) to (RA-12) and/or (RA-1a) to (RA-4f ) and another ring is formed by a structure of formulas (RA-1) to (RA-12), (RA-1a) to (RA-4f) or (RB). Especially in formulas (VI-1) to (VI-22) and/or (VII-1) to (VII-4), the sum of the labels k, j and m is preferably 0, 1, 2 or 3, more preferably Preferably 1 or 2. Further possible examples are: the substituents R, R a , R b , R c , R d , Re , R 1 and R 2 according to the above formula are not combined with the substituents R, R a , R b , R c , The ring atoms of the ring system where Rd , Re , R1 and R2 combine to form a fused aromatic or heteroaromatic ring system. This includes the formation of fused aromatic or heteroaromatic ring systems with possible substituents that may be bonded to the R, R a , R b , R c , R d , Re and R 1 groups. When two groups which may be selected especially from R, R a , R b , R c , R d , Re , R 1 and/or R 2 form a ring system with each other, this ring system may be mono- or polycyclic, Aliphatic, heteroaliphatic, aromatic or heteroaromatic. In this example, the groups that together form the ring system may be adjacent, which means that the groups are bonded to the same carbon atom or to carbon atoms that are directly bonded to each other, or the groups can be further selected from remove each other. In addition, ring systems with substituents R, R a , R b , R c , R d , Re , R 1 and/or R 2 can also be joined to each other via bonds, so that this can result in ring closure. In this example, each corresponding bonding site preferably has substituents R, Ra, Rb , Rc , Rd , Re , R1 and / or R2 . In a preferred configuration, the compounds of the present invention can be represented by formulas (I), (II-1) to (II-42), (III-1) to (III-42), (IV-1) to (IV- 41), (V-1) to (V-8), (VI-1) to (VI-22) and/or (VII-1) to (VII-4) at least one of the structures represented. Preferably comprise formula (I), (II-1) to (II-42), (III-1) to (III-42), (IV-1) to (IV-41), (V-1) To (V-8), (VI-1) to (VI-22) and/or (VII-1) to (VII-4) the compound of the present invention of the structure preferably has not more than 5000 g/mol, relatively Molecular weights are preferably not more than 4000 g/mol, particularly preferably not more than 3000 g/mol, very preferably not more than 2000 g/mol and most preferably not more than 1200 g/mol. Additionally, preferred compounds of the invention are characterized in that they are sublimable. These compounds typically have a molar mass of less than about 1200 g/mol. Preferred aromatic or heteroaromatic ring systems R, R a , R b , R c , R d , Re , Ar ' and/or Ar are selected from phenyl, biphenyl (especially o-, meta- or p-biphenyl), terphenyl (especially o-, m- or p-terphenyl or branched chain terphenyl), tetraphenyl (especially o-, m- or p-tetraphenyl or branched tetraphenyl), fennel which can be bonded via 1, 2, 3 or 4 positions, spirobiscenes which can be bonded via 1, 2, 3 or 4 positions, naphthalene (especially 1- or 2-bonded naphthalene), indole, benzofuran, benzothiophene, carbazole which can be attached via 1, 2, 3, 4 or 9 positions, dibenzofuran which can be attached via 1, 2, 3 or 4 positions, which can be attached via Dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyridine, pyrimidine, tribenzothiophene, quinoline, isoquinoline, quinazoline, Quinoline, phenanthrene, or triphenyl, each of which may be substituted by one or more R or R groups. The following examples are possible with preference: at least one substituent R, Ra , Rb is in each case identical or different and is selected from the group consisting of: H, D, having 3 to 20 carbon atoms branched or cyclic alkyl, alkoxy or thioalkoxy, or an aromatic or heteroaromatic ring system selected from the group of the following formulas Ar-1 to Ar-78; the substituents R, R a , R b preferably forms a fused ring, preferably according to a structure of formulas (RA-1) to (RA-12) or (RB), or the substituents R, R a , R b are in each case identical or different and selected from the group consisting of H, D, or an aromatic or heteroaromatic ring system selected from the group of formulas Ar-1 to Ar-78 below, and/or the Ar' group in each The cases are the same or different and are selected from the group of the following formulas Ar-1 to Ar-78:
Figure 02_image289
Figure 02_image291
Figure 02_image293
Figure 02_image295
Figure 02_image297
Figure 02_image299
Figure 02_image301
Figure 02_image303
wherein R is as defined above, the dotted bond represents the point of attachment, and in addition: Ar are in each case the same or different and have 6 to 18 aromatic ring atoms and can be in each instance A divalent aromatic or heteroaromatic ring system substituted by one or more R 1 groups; A is in each case the same or different and is C(R 1 ) 2 , NR 1 , O or S; p is 0 or 1, where p=0 means that the Ar group does not exist and the corresponding aromatic or heteroaromatic group is directly bonded to the corresponding group; q is 0 or 1, where q=0 means that there is no The A group is bonded at this position, and the R group is instead bonded to the corresponding carbon atom. Here, preference is given to formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar -16), (Ar-40), (Ar-41), (Ar-42), (Ar-43), (Ar-45), (Ar-47), (Ar-57), (Ar-69 ), (Ar-70), (Ar-75), (Ar-78) structures, and particularly preferred for formula (Ar-1), (Ar-2), (Ar-3), (Ar-12 ), (Ar-13), (Ar-14), (Ar-15), (Ar-16) structures. When the aforementioned groups of the structures of formulas (Ar-1) to (Ar-78) have two or more A groups, the possible selection of these groups includes all combinations from the definition of A. In this example, preferred embodiments are those in which one A group is NR 1 and the other A group is C(R 1 ) 2 , or in which two A groups are NR 1 , or in which two A The group is O. When A is NR , the substituent R bonded to the nitrogen atom is preferably an aromatic or heteroaromatic ring having 5 to 24 aromatic ring atoms which may also be substituted by one or more R groups system. In a particularly preferred embodiment, the R substituents are in each case the same or different and are aromatic or aromatic with 6 to 24, especially 6 to 18, aromatic ring atoms. Heteroaromatic ring systems which do not have any fused aryl and any fused heteroaryl groups in which two or more aromatic or heteroaromatic 6-membered ring groups are directly fused to each other, and which may also be present in each Examples are substituted with one or more R2 groups. Preference is given to phenyl, biphenyl, terphenyl and tetraphenyl having the bonding patterns listed above as Ar-1 to Ar-11, wherein these structures can be transformed via one or more R groups Not R 1 substituted, but preferably unsubstituted. Further preference is given to the three pyrimidines, pyrimidines and quinazolines listed above as Ar-47 to Ar-50, Ar-57 and Ar-58, wherein these structures can be modified by one or more R groups other than R 1 substituted. Preferred substituents R, Ra , Rb , Rc , Rd and Re are illustrated subsequently. In a preferred embodiment of the present invention, R, R a , R b are in each case the same or different and are selected from the group consisting of: H, D, F, CN, NO 2 , Si(R 1 ) 3 , B(OR 1 ) 2 , linear alkyl having 1 to 20 carbon atoms or branched or cyclic alkyl having 3 to 20 carbon atoms, wherein the alkyl can be in each Examples are substituted by one or more R 1 groups, or have 5 to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms and can be substituted by one or more R 1 groups in each example Substituted aromatic or heteroaromatic ring systems. In a further preferred embodiment of the present invention, the substituents R, R a , R b are in each case the same or different and are selected from the group consisting of H, D, F, with 1 A straight-chain alkyl group of up to 20 carbon atoms or a branched or cyclic alkyl group of 3 to 20 carbon atoms, wherein the alkyl group may in each case be substituted by one or more R groups, or have 5 An aromatic or heteroaromatic ring system of up to 60 aromatic ring atoms, preferably 5 to 40 aromatic ring atoms, which may in each case be substituted by one or more R groups. Possible further examples are the following: at least one substituent R, Ra , Rb is in each case the same or different and is selected from the group consisting of: H, D, having 6 to 30 aromatic ring atoms and may be substituted by one or more R 1 groups, an aromatic or heteroaromatic ring system, or an N(Ar′) 2 group. In a further preferred embodiment of the present invention, the substituents R, R a , R b , R c , R d form according to formulas (RA-1) to (RA-12), (RA-1a) to ( The rings of the structure of RA-4f) or (RB), or R, R a , R b are in each case the same or different and are selected from the group consisting of H, D, having 6 to 30 An aromatic or heteroaromatic ring system which is an aromatic ring atom and which may be substituted by one or more R1 groups, or an N(Ar') 2 group. The substituents R, Ra , Rb are preferably in each case the same or different and are selected from the group consisting of H or having 6 to 24 aromatic ring atoms, preferably having 6 to 18 aromatic ring atoms, more preferably an aromatic or heteroaromatic system with 6 to 13 aromatic ring atoms, each of which may be substituted by one or more R groups. The following examples may be preferred: at least one substituent R, R a , R b , R c , R d is selected from the group consisting of phenyl, biphenyl, terphenyl, tetraphenyl, fennel, spirodipic, naphthalene, Indole, benzofuran, benzothiophene, carbazole, dibenzofuran, dibenzothiophene, indenocarbazole, indolocarbazole, pyridine, pyrimidine, pyridine, pyrimidine, trisulfone, quinoline , isoquinoline, quinazoline, quinoline, phenanthrene, and triphenyl, each of which may be substituted by one or more R groups. Here more particularly by the word "substituent" is meant that R, R a , R b , R c , R d are not H. In addition, if there are two or more substituents selected from the mentioned aromatic or heteroaromatic groups, the substituents R, R a , R b , R c , R d may be the same or different of. In a further embodiment, the following examples may be: at least one substituent R, R a , R b , R c , R d is selected from o-biphenyl, o,o'-terphenyl, o,o ', p-tetraphenyl, 4,6-diphenylpyrimidin-2-yl, 4,6-diphenyltriphenyl-2-yl, naphthalene, phenanthrene, fennel, spirobis, triphenyl, anthracene , benzanthracene, stilbene and/or pyrene, each of which may be substituted by one or more R groups. Preferred here are spirobistilbene, o-biphenyl, o,o'-terphenyl, o,o',p-tetraphenyl, 4,6-diphenylpyrimidin-2-yl, 4,6 -Diphenyltri-2-yl. If there are two or more substituents selected from the aromatic substituents mentioned above, the substituents R, R a , R b , R c , R d may be the same or different. It is selected from o-biphenyl, o, o'-terphenyl, o, o', p-tetraphenyl, 4,6-diphenylpyrimidin-2-yl, 4,6-diphenyltriphenyl Structures/compounds of the group of -2-yl, naphthalene, phenanthrene, phenanthrene, spirobisyl, triphenylene, anthracene, benzanthracene, fenthrene and/or pyrene are particularly suitable as electron transport materials and/or matrix materials. With regard to the substituents R c , R d , the statements of preference as stated above for the substituents R , R a , R b with the aforementioned restrictions apply correspondingly. Especially possible are the following examples: at least one substituent R c , R d is in each case the same or different and is selected from the group consisting of: having 6 to 30 aromatic ring atoms and which can be substituted by one or more An aromatic or heteroaromatic ring system substituted by R1 groups and an N(Ar') 2 group. Further possible examples are that the substituents R c , R d form a fused ring, preferably according to the structures of formulas (RA-1) to (RA-12) or (RB), or that the substituents R c , R d are in are in each case the same or different and are selected from the group consisting of an aromatic or heteroaromatic ring system having 6 to 30 aromatic ring atoms which may be substituted by one or more R groups and N(Ar') 2 group. The following example may be more preferable: the substituents R c , R d are the same or different in each case and represent 6 to 30 aromatic ring atoms and can be selected from the ones shown above by one or more Aromatic or heteroaromatic ring systems substituted by R groups of formulas (Ar- 1 ) to (Ar-78). In a preferred embodiment of the present invention, R e is in each case the same or different and is selected from the group consisting of: straight-chain alkyl having 1 to 20 carbon atoms or having 3 to A branched or cyclic alkyl group of 20 carbon atoms, wherein the alkyl group may in each case be substituted by one or more R groups, or have 5 to 60 aromatic ring atoms, preferably 5 to 40 Aromatic or heteroaromatic ring systems which may in each case be substituted by one or more R groups of aromatic ring atoms . In a further preferred embodiment of the present invention, R e is in each case the same or different and is selected from the group consisting of straight-chain alkyl having 1 to 10 carbon atoms or having 3 A branched or cyclic alkyl group of up to 10 carbon atoms, wherein the alkyl group may in each instance be substituted by one or more R groups, have 6 to 30 aromatic ring atoms and may be substituted by one or more An aromatic or heteroaromatic ring system substituted with an R2 group. Re is more preferably in each case the same or different and is selected from the group consisting of straight chain alkyl having 1 to 5 carbon atoms, or branched chain having 3 to 5 carbon atoms or Cyclic alkyl, wherein the alkyl can be substituted by one or more R groups in each example, or have 6 to 24 aromatic ring atoms, preferably 6 to 18 aromatic ring atoms, more preferably is an aromatic or heteroaromatic ring system of 6 to 13 aromatic ring atoms which may in each case be substituted by one or more R2 groups. In a preferred embodiment of the present invention, R e is in each case the same or different and is selected from the group consisting of: straight-chain alkyl having 1 to 6 carbon atoms or having 3 to A cyclic alkyl group of 6 carbon atoms, wherein the alkyl group may be substituted by one or more R groups in each instance, or have 6 to 24 aromatic ring atoms and may be substituted by one or more R groups in each instance An aromatic or heteroaromatic ring system substituted by two R groups; meanwhile, two R groups can also be formed together to form a ring system. R e are more preferably in each case the same or different and are selected from the group consisting of straight-chain alkyl groups having 1, 2, 3 or 4 carbon atoms or alkyl groups having 3 to 6 carbon atoms Branched or cyclic alkyl, wherein the alkyl may in each case be substituted by one or more R groups, but is preferably unsubstituted, or has 6 to 12 aromatic ring atoms, especially 6 aromatic ring atoms and may in each case be substituted by one or more preferably non-aromatic R groups, but preferably unsubstituted aromatic ring systems; meanwhile, two R groups may Together they form a ring system. R e are optimally in each case the same or different and are selected from the group consisting of straight-chain alkyl having 1, 2, 3 or 4 carbon atoms or alkyl having 3 to 6 carbon atoms branched chain alkyl. R e is most preferably methyl or phenyl, where two phenyl groups may be taken together to form a ring system, preferably methyl rather than phenyl. Preferred aromatic or heteroaromatic ring systems represented by substituents R, Ra, Rb , Rc , Rd , Re or Ar or Ar ' are selected from phenyl, biphenyl (especially o- , m- or p-biphenyl), terphenyl (especially o-, m- or p-terphenyl or branched terphenyl), tetraphenyl (especially o-, m- or p- Tetraphenyl or branched tetraphenyl), fennel which can be linked via 1, 2, 3 or 4 positions, spirodicene which can be linked via 1, 2, 3 or 4 positions, naphthalene (especially via 1- or 2- bonded naphthalene), indole, benzofuran, benzothiophene, carbazole which can be attached via 1, 2, 3 or 4 positions, dibenzofuran which can be attached via 1, 2, 3 or 4 positions, Dibenzothiophenes, indenocarbazoles, indolocarbazoles, pyridines, pyrimidines, pyridines, pyrimidines, tribenzothiophenes, quinolines, isoquinolines, quinazolines joined via the 1, 2, 3 or 4 positions , quinoline, phenanthrene or triphenyl, each of which may be substituted by one or more R, R 1 or R 2 groups. The structures Ar-1 to Ar-78 listed above are particularly preferred, preferably the formulas (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16), (Ar-69), (Ar-70), (Ar-75) structures, and particularly preferred for the formula (Ar-1), (Ar-2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) formula (Ar-1), (Ar -2), (Ar-3), (Ar-12), (Ar-13), (Ar-14), (Ar-15), (Ar-16) structures. With respect to structures Ar-1 to Ar-78, it should be stated that these are shown with the substituent R1 . In the case of the ring system Ar, the substituents R 1 should be replaced by R, and in the case of Re the substituents R 1 should be replaced by R 2 . Other suitable R, R a , R b , R c , R d groups are groups of formula -Ar 4 -N(Ar 2 )(Ar 3 ), where Ar 2 , Ar 3 and Ar 4 are in each case are the same or different and are aromatic or heteroaromatic ring systems having 5 to 24 aromatic ring atoms which may in each case be substituted by one or more R groups. The total number of aromatic ring atoms in Ar 2 , Ar 3 and Ar 4 here does not exceed 60, and preferably does not exceed 40. In this example, Ar 4 and Ar 2 may also be bonded to each other and/or Ar 2 and Ar 3 may be bonded to each other with a group selected from C(R 1 ) 2 , NR 1 , O and S. Preferably Ar 4 and Ar 2 are bonded to each other and Ar 2 and Ar 3 are bonded to each other in respective ortho positions with respect to the bond connecting the nitrogen atom. In a further embodiment of the invention none of the Ar 2 , Ar 3 and Ar 4 groups are bonded to each other. Ar is preferably an aromatic or heteroaromatic ring having 6 to 24 aromatic ring atoms, preferably 6 to 12 aromatic ring atoms and which may in each case be substituted by one or more R groups system. Ar is more preferably selected from the group consisting of o-, m- or p-phenylene or o-, m- or p-biphenyl, each of which can be modified by one or more R groups substituted, but preferably unsubstituted. Ar 4 is most preferably an unsubstituted phenylene group. Ar 2 and Ar 3 are preferably in each case the same or different and are aromatic or heteroaromatic having 6 to 24 aromatic ring atoms which may in each case be substituted by one or more R groups aromatic ring system. Particularly preferred Ar and Ar groups are in each case the same or different and are selected from the group consisting of benzene, o-, m- or p-biphenyl, o-, m- or p -Terphenyl or branched terphenyl, o-, m- or p-tetraphenyl or branched terphenyl, 1-, 2-, 3- or 4-fenyl, 1-, 2-, 3 - or 4-spirodiperyl, 1- or 2-naphthyl, indole, benzofuran, benzothiophene, 1-, 2-, 3- or 4-carbazole, 1-, 2-, 3- or 4-dibenzofuran, 1-, 2-, 3- or 4-dibenzothiophene, indenocarbazole, indolocarbazole, 2-, 3- or 4-pyridine, 2-, 4- or 5-pyrimidine, pyrimidine, pyridine, triphenyl, phenanthrene, or triphenyl, each of which may be substituted by one or more R groups. Ar and Ar are optimally in each case the same or different and are selected from the group consisting of benzene, biphenyl (especially o-, m- or p-biphenyl), terphenyl (especially o-, m- or p-terphenyl or branched terphenyl), tetraphenyl (especially o-, m- or p-tetraphenyl or branched terphenyl), terphenyl (especially is 1-, 2-, 3- or 4-oxo) or spirobioxa (especially 1-, 2-, 3- or 4-spirobioxa). In a further preferred embodiment of the invention, R are in each case the same or different and are selected from the group consisting of H, D, F, CN, having 1 to 10 carbon atoms or a branched or cyclic alkyl group having 3 to 10 carbon atoms, wherein the alkyl group may in each instance be substituted by one or more R groups, or have 6 to 24 aromatic Ring atoms and aromatic or heteroaromatic ring systems which may in each case be substituted by one or more R2 groups. In a particularly preferred embodiment of the invention, R are in each case the same or different and are selected from the group consisting of: H, having 1 to 6 carbon atoms, especially having 1, 2 , a linear alkyl group of 3 or 4 carbon atoms or a branched or cyclic alkyl group having 3 to 6 carbon atoms, wherein the alkyl group may be substituted by one or more R groups, but preferably not A substituted, or aromatic or heteroaromatic ring system having 6 to 13 aromatic ring atoms which may in each case be substituted by one or more R groups, but is preferably unsubstituted. In a further preferred embodiment of the present invention, R is in each case the same or different and is H, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms , which may be substituted with an alkyl group having 1 to 4 carbon atoms, but is preferably unsubstituted. Meanwhile, in the compounds of the present invention processed by vacuum evaporation, the alkyl group preferably has not more than 5 carbon atoms, more preferably not more than 4 carbon atoms, most preferably not more than 1 carbon atom. As regards compounds processed from solution, suitable compounds are also those substituted by alkyl groups having up to 10 carbon atoms, especially branched chain alkyl groups, or those substituted by oligoaryl groups, such as ortho-, meta- or Compounds substituted with p-terphenyl or branched terphenyl or tetraphenyl groups. It may further be the following example: the compound comprises exactly two or exactly three formulas (I), (II-1) to (II-42), (III-1) to (III-41), (IV-1) to Structures of (IV-41), (V-1) to (V-8), (VI-1) to (VI-22) and/or (VII-1) to (VII-4). In a preferred configuration, the compound is selected from compounds of formula (D-1) or (D-2):
Figure 02_image305
wherein the L group is a linking group, preferably a bond or an aromatic or heteroaryl having 5 to 40, preferably 5 to 30, aromatic ring atoms which may be substituted by one or more R groups A group of ring systems, and the other symbols used have the definitions given above, especially for formula (I). In a further preferred embodiment of the invention, L is a bond or an aromatic or heteroaromatic ring system having 5 to 14 aromatic or heteroaromatic ring atoms, preferably 6 to 12 carbons atom and may be substituted by one or more R 1 groups, but preferably unsubstituted aromatic ring system, wherein R 1 may have the definition given above, especially in formula (I). L is more preferably an aromatic ring system having 6 to 10 aromatic ring atoms or a heteroaromatic ring system having 6 to 13 heteroaromatic ring atoms, each of which may be modified by one or more R groups substituted, but preferably unsubstituted, wherein R 2 may have the definition given above, especially for formula (I). The symbols L shown in formula (D2) are more preferably in each case the same or different and are bonds or have 5 to 24 ring atoms, preferably 6 to 13 ring atoms, more preferably An aryl or heteroaryl group of 6 to 10 ring atoms, such that an aromatic or heteroaromatic group of an aromatic or heteroaromatic ring system is bonded directly to the respective atom of another group, i.e. via an aromatic or heteroaromatic An atom of a heteroaromatic group. Also possible are the following examples: the L group shown in formula (D2) contains no more than four, preferably no more than three, more preferably no more than two fused aromatic and/or heteroaryl An aromatic ring system that is a 6-membered ring and preferably does not contain any fused aromatic or heteroaromatic ring systems. Therefore, naphthyl structures are preferred over anthracene structures. In addition, perylene, spirodifenyl, dibenzofuranyl and/or dibenzothienyl structures are preferred over naphthyl structures. Particular preference is given to structures that do not have fused structures, such as phenyl, biphenyl, terphenyl and/or tetraphenyl structures. Examples of suitable aromatic or heteroaromatic ring systems L are selected from the group consisting of ortho-, m- or p-phenylene, ortho-, m- or p-biphenylene, biphenylene Triphenylene (especially branched-chain triphenylene), bis-tetraphenylene (especially branched-chain tetraphenylene), pyrene, spirobifluorenyl (spirobifluoronylene), dibenzofuryl ( dibenzofuranylene ), dibenzothienylene and carbazolylene, each of which may be substituted by one or more R 1 groups, but are preferably unsubstituted. The aforementioned preferred implementation forms can be combined with each other as required within the limited scope defined in Claim 1. In a particularly preferred embodiment of the present invention, the aforementioned preferences occur simultaneously. Examples of preferred compounds according to the embodiments detailed above are those shown in the following table:
Figure 02_image307
Figure 02_image309
Figure 02_image311
Figure 02_image313
Figure 02_image315
Figure 02_image317
Figure 02_image319
Figure 02_image321
Figure 02_image323
Figure 02_image325
Figure 02_image327
Figure 02_image329
Figure 02_image331
Figure 02_image333
Figure 02_image335
Figure 02_image337
Figure 02_image339
Figure 02_image341
Preferred embodiments of the compounds of the present invention are described in detail in the Examples, and these compounds are used alone or in combination with other compounds for all purposes of the present invention. If the conditions specified in claim 1 are met, the aforementioned preferred implementation forms can be combined with each other as required. In a particularly preferred embodiment of the present invention, the above-mentioned preferred embodiments are applicable at the same time. The compounds according to the invention are prepared in principle in various ways. However, the methods described below have been found to be particularly suitable. Therefore, the present invention further provides a process for the preparation of the compounds of the present invention, wherein the basic skeleton of a precursor having at least one of the W a groups or one of the W a groups is synthesized and then by means of nucleophilic aromatic Substitution or coupling reactions introduce aromatic or heteroaromatic groups. Suitable compounds comprising a basic skeleton with a W a group are in many cases commercially available, and the starting compounds detailed in the examples were obtained by known methods and reference is hereby made. These compounds can be reacted with other compounds in known coupling reactions, the prerequisites for this purpose being that those skilled in the art are known and given the support of those skilled in the art in carrying out these reactions by the specifications detailed in the examples. . All particularly suitable and preferred coupling reactions leading to CC bond formation and/or CN bond formation are those according to BUCHWALD, SUZUKI, YAMAMOTO, STILLE, Heck (HECK), Negishi (NEGISHI), Sonogashira (SONOGASHIRA) and Hiyama (HIYAMA) responses. These reactions are well known and the examples will provide further hints to those skilled in the art. The principles of the preparation methods detailed above are known in principle from the literature for analogous compounds and can be easily adapted by a person skilled in the art to prepare the compounds of the invention. More information can be found in the examples. With these methods (if necessary followed by purification, eg recrystallization or sublimation) it is possible to obtain compounds of the invention in high purity, preferably greater than 99% (determined by means of 1 H NMR and/or HPLC). The compounds of the invention may also be mixed with polymers. It is also possible to covalently incorporate such compounds into polymers. This is especially possible with compounds substituted with reactive leaving groups such as bromine, iodine, chlorine, boronic acid or boronic esters, or with reactive polymerizable groups such as olefins or oxygens. These may find use as monomers for the manufacture of corresponding oligomers, dendrimers or polymers. Oligomerization or polymerisation is preferably effected via halogen functionality or boronic acid functionality or via polymerisable groups. It is additionally possible to crosslink polymers via groups of this type. The compounds and polymers of the invention can be used in the form of crosslinked or uncrosslinked layers. The present invention therefore further provides oligomers, polymers or dendrimers containing the structure of formula (I) detailed above and preferred embodiments of this formula or one or more of the compounds of the present invention, Wherein the compounds of the present invention or the structure of formula (I) and preferred embodiments of this formula have one or more bonds to polymers, oligomers or dendrimers present. According to the structure of formula (I) and preferred embodiments of this formula or the linkage of compounds, these thus form side chains of oligomers or polymers or are bound within the main chain. The polymers, oligomers or dendrimers may be conjugated, partially conjugated or non-conjugated. Oligomers or polymers may be linear, branched or dendritic. With regard to the recurring units of the compounds of the invention in oligomers, dendrimers and polymers, the same preferences as above apply. The monomers of the invention used to prepare oligomers or polymers are homopolymerized or copolymerized with other monomers. It is preferred that the units of formula (I) or the preferred embodiments described above and below are 0.01 to 99.9 mol%, preferably 5 to 90 mol%, more preferably 20 to 80 mol% Existing copolymers. Suitable and preferred co-monomer systems for forming the basic backbone of the polymer are selected from the group consisting of terpene (for example according to EP 842208 or WO 2000/022026), spirobistilbene (for example according to EP 707020, EP 894107 or WO 2006/061181 ), parabiscene Phenyl (eg according to WO 92/18552), carbazole (eg according to WO 2004/070772 or WO 2004/113468), thiophene (eg according to EP 1028136), dihydrophenanthrene (eg according to WO 2005/014689), cis- and trans-indenofluorene (eg according to WO 2004/041901 or WO 2004/113412), ketone (eg according to WO 2005/040302), phenanthrene (eg according to WO 2005/104264 or WO 2007/017066) or other pluralities of these units . The polymers, oligomers and dendrimers may still contain other units, such as hole transport units (especially those based on triarylamines) and/or electron transport units. In addition, particular attention is paid to the compounds according to the invention which are characterized by a high glass transition temperature. In this regard, particular preference is given to compounds of the present invention comprising formula (I) or the structures of the preferred embodiments described above and below, which have at least A glass transition temperature of 70°C, more preferably at least 110°C, even better at least 125°C, and especially at least 150°C. The formulation of the compounds of the invention is necessary for processing the compounds of the invention from the liquid phase, for example by spin-coating methods or by printing methods. Such formulations may be, for example, solutions, dispersions or emulsions. For this purpose it may be preferred to use a mixture of two or more solvents. Suitable and preferred solvents are e.g. toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetralin, veratrole, THF, methyl-THF, THP , chlorobenzene, dioxane, phenoxytoluene (especially 3-phenoxytoluene), (-)-fenzyl ketone, 1,2,3,5-tetramethylbenzene, 1,2,4,5 -tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-Dimethylanisole, 3,5-Dimethylanisole, Acetophenone, α-Terpineol, Benzothiazole, Butyl Benzoate, Cumene, Cyclohexanol, Cyclohexanone , cyclohexylbenzene, decahydronaphthalene, dodecylbenzene, ethyl benzoate, indane, NMP, p-isopropyltoluene, phenetole, 1,4-diisopropylbenzene, di Anisole, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethyl ether Glyme, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1,1-bis(3,4-dimethylphenyl)ethane, 2-methyl Biphenyl, 3-methylbiphenyl, 1-methylnaphthalene, 1-ethylnaphthalene, ethyl octanoate, diethyl sebacate, octyl octanoate, heptylbenzene, menthyl isovalerate ), cyclohexyl hexanoate or a mixture of these solvents. The present invention thus further provides formulations or compositions comprising at least one compound according to the invention and at least one other compound. The other compound may be, for example, a solvent, especially one of the aforementioned solvents or a mixture of such solvents. If the other compounds include a solvent, this mixture is referred to herein as a formulation. The further compound can alternatively be at least one other organic or inorganic compound which is likewise used in electronic devices, for example emitters and/or matrix materials, wherein these compounds differ from the compounds according to the invention. Suitable emitters and matrix materials are listed below in relation to organic electroluminescent devices. Other compounds may also be polymers. The present invention therefore further provides compounds comprising at least one compound of formula (I)
Figure 02_image343
The symbols used therein have the definitions given above, preferably at least one compound of the invention or an oligomer, polymer or dendrimer comprising a structure of formula (I), and at least one other organic functional Composition of materials. Functional materials are generally organic or inorganic materials introduced between the anode and cathode. The organic functional material is preferably selected from the group consisting of: fluorescent emitters, phosphorescent emitters, emitters exhibiting TADF (Thermally Activated Delayed Fluorescence), host materials, electron transport materials, electron injection materials, electrical Hole-conducting materials, hole-injecting materials, electron-blocking materials, hole-blocking materials, wide-bandgap materials, and n-dopants. The present invention further provides the compound of formula (I)
Figure 02_image345
The symbols used therein have the definitions given above, preferably compounds of the present invention or oligomers, polymers or dendrimers comprising structures of formula (I) in electronic devices, especially in organic electroluminescent devices It is preferably used as a luminous body, more preferably as a green, red or blue luminous body. In this instance, the compounds of the invention preferably exhibit fluorescent properties and thus preferentially provide fluorescent emitters. The following examples may be preferred: using formulas (II-2) to (II-8), (II-17) to (II-23), (III-2) to (III-8), (III-17 ) to (III-23), (IV-2) to (IV-8), (IV-17) to (IV-23), (V-1), (V-2), (V-5) and /or the structure/compound of (V-6) as an emitter. In addition, compounds of formula (I) or oligomers, polymers or dendrimers comprising structures of formula (I) can be used as host materials and/or electron transport materials. The following examples may be preferred: use of structures/compounds with anthracene groups (Ar-76) to (Ar-78), preferably (Ar-78), and/or formulas (II-9), (II -10), (II-24), (II-25), (III-9), (III-10), (III-24), (III-25), (IV-9), (IV-10 ), (IV-24) and/or (IV-25) compounds as electron transport materials and/or matrix materials. The present invention further provides a compound comprising at least one formula (I)
Figure 02_image347
The symbols used therein have the definitions given above, preferably the compounds of the invention or electronic devices comprising oligomers, polymers or dendrimers of the structure of formula (I). An electronic device in the context of the present invention is a device comprising at least one layer comprising at least one organic compound. The component may also include inorganic materials or other layers formed entirely from inorganic materials. The electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs, sOLEDs, PLEDs, LECs, etc.), preferably organic light emitting diodes (OLEDs), organic light emitting devices based on small molecules Diode (sOLED), polymer-based organic light-emitting diode (PLED), light-emitting electrochemical cell (LEC), organic laser diode (O-laser), organic plasmon light-emitting device ( DM Koller et al. Nature Photonics 2008, 1-4), Organic Integrated Circuit (O-IC), Organic Field Effect Transistor (O-FET), Organic Thin Film Transistor (O-TFT), Organic Light Emitting Transistor ( O-LET), organic solar cells (O-SC), organic optical detectors, organic photoreceptors, organic field quenching devices (O-FQD) and organic electrical sensors, preferably organic electroluminescent devices (OLED, sOLED, PLED, LEC, etc.), more preferably organic light-emitting diodes (OLED), small molecule-based organic light-emitting diodes (sOLED), polymer-based organic light-emitting diodes (PLED), Especially phosphorescent OLEDs. An organic electroluminescent device includes a cathode, an anode and at least one light emitting layer. In addition to these layers, it may also comprise other layers, such as in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers , an electron blocking layer and/or a charge generating layer. It is also possible, for example, to introduce an interlayer having an exciton-blocking function between two emitting layers. However, it should be noted that each of these layers does not necessarily have to be present. In this example, the organic electroluminescent device may contain one light-emitting layer or contain multiple light-emitting layers. If several emitting layers are present, these layers preferably have a plurality of emission maxima totaling between 380 nm and 750 nm, so that white emission is generated overall; in other words, the fluorescent or phosphorescent Various emitting compounds are used in the emitting layer. Especially preferred are systems with three emitting layers, three of which exhibit blue, green and orange or red emission. The organic electroluminescent device of the present invention can also be a tandem electroluminescent device, especially a white light-emitting OLED. The compounds according to the invention can be used in different layers depending on the precise structure. Preference is given to organic electroluminescence of structures/compounds of the formula (I) or the preferred embodiments described in detail above as luminescent bodies, preferably as red, green or blue luminous bodies, contained in the light-emitting layer device. Very preferred is an organic electroluminescent device comprising the structure/compound of formula (I) or the preferred embodiments detailed above as a blue fluorescent emitter in the light-emitting layer. Especially preferred here are formulas (II-2) to (II-8), (II-17) to (II-23), (III-2) to (III-8), (III-17) to ( III-23), (IV-2) to (IV-8), (IV-17) to (IV-23), (V-1), (V-2), (V-5) and/or ( Structures/compounds of V-6). When the compounds according to the invention are used as emitters in the emitting layer, preference is given to using matrix materials (also referred to as host materials) which are known per se to be suitable. Preferred mixtures of compounds according to the invention and matrix material contain between 99% by volume and 1% by volume, preferably between 98% by volume and 10% by volume, based on the total mixture of emitter and matrix material, More preferred is between 97% by volume and 60% by volume, and especially between 95% by volume and 80% by volume of matrix material. The mixture correspondingly contains between 1% by volume and 99% by volume, preferably between 2% by volume and 90% by volume, more preferably between 3% by volume, based on the total mixture of emitter and matrix material and 40% by volume, and in particular between 5% by volume and 20% by volume of the emitter. Suitable matrix materials which can be used in combination with the compounds according to the invention are aromatic ketones, aromatic phosphine oxides or aromatic arsonites or phosphine (for example according to WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/ 006680), triarylamines, carbazole derivatives (such as CBP (N,N-biscarbazolylbiphenyl) or in WO 2005/039246, US 2005/0069729, JP 2004/288381, EP 1205527, WO 2008/086851 or the carbazole derivatives disclosed in WO 2013/041176), indolocarbazole derivatives (for example according to WO 2007/063754 or WO 2008/056746), indenocarbazole derivatives (for example according to WO 2010/136109, WO 2011/000455, WO 2013/041176 or WO 2013/056776), azacarbazole derivatives (eg according to EP 1617710, EP 1617711, EP 1731584, JP 2005/347160), bipolar matrix materials (eg according to WO 2007/ 137725), silanes (e.g. according to WO 2005/111172), azaboroles or borates (e.g. according to WO 2006/117052), trioxane derivatives (e.g. according to WO 2007/063754, WO 2008/056746, WO 2010/015306, WO 2011/057706, WO 2011/060859 or WO 2011/060877), zinc complexes (eg according to EP 652273 or WO 2009/062578), diazasilole or tetraazasilole Tetraazasilole derivatives (for example according to WO 2010/054729), diazaphosphole derivatives (for example according to WO 2010/054730), bridged carbazole derivatives (for example according to WO 2011/042107, WO 2011 /060867, WO 2011/088877 and WO 2012/143080), triphenyl derivatives (eg according to WO 2012/048781), dibenzofuran derivatives (eg according to WO 2015/169412, WO 2016/015810, WO 2016/ 023608, WO 2017/148564 or WO 2017/148565) or biscarbazole (eg according to JP 3139321 B2). In addition, the co-hosts used may be compounds which participate somewhat, but not to a significant extent, in charge transport, as described, for example, in WO 2010/108579. Particularly suitable as co-matrix materials in combination with the compounds according to the invention are compounds which have a large energy band gap and which themselves participate, if at all, in the charge transport of the emitting layer, at least not to a significant extent. These materials are preferably pure hydrocarbons. Examples of such materials can be found eg in WO 2009/124627 or WO 2010/006680. In a preferred configuration, the compound containing the structure/compound of the formula (I) or the preferred embodiment described in detail above as an emitter is preferably combined with one or more phosphorescent materials (triplet emitter ) and/or in combination with compounds that are TADF (Thermally Activated Delayed Fluorescent) host materials. Here it is preferred to form a superfluorescent system as described in WO 2012/133188 and/or a superphosphorescent system as described in 2017271611. This combination is a preferred composition according to the present invention. WO 2015/091716 A1 and WO 2016/193243 A1 disclose OLEDs containing both phosphorescent compounds and fluorescent emitters in the emitting layer, wherein energy is transferred from the phosphorescent compounds to the fluorescent emitters (hyperphosphorescence). In this context, phosphorescent compounds can thus function as host materials. As known by those skilled in the art, the host material has higher singlet and triplet energy than the emitter, so that the energy from the host material is also transferred to the emitter with maximum efficiency. Systems disclosed in the prior art do have this energy relationship. Phosphorescence in the context of the present invention is understood to mean luminescence from excited states with a higher spin multiplicity (ie spin state > 1), especially luminescence from excited triplet states. In the context of the present application, all luminescent complexes with transition metals or lanthanides, in particular all iridium, platinum and copper complexes, are to be regarded as phosphorescent compounds. Suitable phosphorescent compounds (=triplet emitters) are especially those which, when properly excited, emit light preferably in the visible region and also contain at least one atomic number greater than 20, preferably greater than 38 and less than 84, more preferably Compounds with more than 56 and less than 80 atoms, especially metals with this atomic number. Preferred phosphorescent emitters used are compounds containing copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium or platinum. Examples of the above-mentioned luminophores can be found in the applications WO 00/70655, WO 2001/41512, WO 2002/02714, WO 2002/15645, EP 1191613, EP 1191612, EP 1191614, WO 05/033244, WO 05/ 019373, US 2005/0258742, WO 2009/146770, WO 2010/015307, WO 2010/031485, WO 2010/054731, WO 2010/054728, WO 2010/086089, WO 2010/0998002, WO 207 032626, WO 2011/066898, WO 2011/157339, WO 2012/007086, WO 2014/008982, WO 2014/023377, WO 2014/094961, WO 2014/094960, WO 2015/036074, WO 2015/15 117718, WO 2016/015815, WO 2016/124304, WO 2017/032439, WO 2018/011186, WO 2018/001990, WO 2018/019687, WO 2018/019688, WO 2018/041769, WO 4018/ 069196, WO 2018/069197, WO 2018/069273, WO 2018/178001, WO 2018/177981, WO 2019/020538, WO 2019/115423, WO 2019/158453 and WO 2019/179909. In general all phosphorescent complexes as used in phosphorescent electroluminescent devices according to the prior art and known to those skilled in the art of organic electroluminescent devices are suitable and can be used by those skilled in the art without exercising innovative skills Other phosphorescent complexes. The compounds of the present invention can preferably be used in combination with TADF host materials and/or TADF emitters as explained above. A method called thermally activated delayed fluorescence (TADF) is described eg by BH Uoyama et al. Nature 2012, Vol. 492, 234. In order to be able to carry out this method, a small singlet-triplet separation ΔE(S 1 −T 1 ), for example less than about 2000 cm −1 , is required in the emitter. In order to turn on the in principle spin-forbidden
Figure 02_image349
Transitions, in addition to emitters, make it possible to provide other compounds in a matrix with strong spin-orbit coupling, enabling intersystem switching via spatial proximity and thus possible interactions between molecules, or by means of luminescent Spin-orbit coupling occurs due to the presence of metal atoms in the bulk. Other sources of valuable information on hyperfluorescence systems include WO2012/133188 (Idemitsu), WO2015/022974 (Kyushu Univ.), WO2015/098975 (Idemitsu), WO2020/053150 (Merck) and DE202019005189 (Merck). Other sources of valuable information on ultra-phosphorescent systems include WO2015/091716 A1, WO2016/193243 A1 (BASF), WO01/08230 A1 (Princeton Univ. (Mark Thompson)), US2005/0214575A1 (Fuji), WO2012/079673 (Merck), WO2020/053314 (Merck) and WO2020/053315 (Merck). In a further embodiment of the present invention, the organic electroluminescent device of the present invention does not contain any separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, which means Means that the emitting layer directly adjoins the hole injection layer or the anode, and/or the emissive layer directly adjoins the electron transport layer or the electron injection layer or the cathode, as described for example in WO 2005/053051. It is additionally possible to use the same or similar metal complexes as the metal complexes in the emitting layer as hole transport or hole injection materials directly adjacent to the emitting layer, as described for example in WO 2009/030981. Also preferred is an organic electroluminescent device comprising the structure/compound of formula (I) or the preferred embodiments detailed above as the electron transport material in the electron conduction layer. Particularly preferred here are compounds having an anthracene group, preferably a group of formulas (Ar-76) to (Ar-78), preferably (Ar-78), and/or formula (II-9) , (II-10), (II-24), (II-25), (III-9), (III-10), (III-24), (III-25), (IV-9), ( Structures/compounds of IV-10), (IV-24) and/or (IV-25). In the other layers of the organic electroluminescent device according to the invention, it is possible to use any materials as are generally used according to the prior art. Those skilled in the art are therefore able to use any material known for organic electroluminescent devices in combination with the structure/compound of formula (I) or the preferred embodiments described above without using innovative skills. Also preferred are organic electroluminescent devices characterized by one or more layers being coated by the sublimation method. In this case, the material is applied by vapor deposition in a vacuum sublimation system at an initial pressure below 10 −5 mbar, preferably below 10 −6 mbar. However, even lower initial pressures, for example below 10 −7 mbar, are also possible. Likewise, preference is given to organic electroluminescent devices featuring one or more layers coated by the OVPD (Organic Vapor Phase Deposition) method or supplemented by carrier gas sublimation. In this example, the material is applied at a pressure between 10 −5 mbar and 1 bar. A particular example of this method is the OVJP (Organic Vapor Jet Printing) method, in which the material is applied directly with a nozzle and thus structured. In addition, preference is given to organic electroluminescent devices featuring one or more layers fabricated from solution, for example by spin-coating or by any printing method, such as screen printing, quick-dry printing, lithography, LITI (photo induced thermal imaging, thermal transfer printing), inkjet printing or nozzle printing. Soluble compounds are necessary for this purpose, which are obtained, for example, by suitable substitutions. Formulations employing compounds of formula (I) or preferred embodiments thereof detailed above are novel. The present invention therefore further provides formulations comprising at least one solvent and a compound according to formula (I) or its preferred embodiments detailed above. In addition, hybrid methods are possible in which, for example, one or more layers are applied from solution and one or more other layers are applied by vapor deposition. Those skilled in the art generally know the methods and can apply them to organic electroluminescent devices comprising the compounds of the invention without exercising innovative skills. The compounds according to the invention and the organic electroluminescent devices according to the invention are particularly characterized by an improved lifetime over the prior art. At the same time, other electronic properties of the electroluminescent device, such as efficiency or operating voltage, remain at least as good. In a further variant, the compounds according to the invention and the organic electroluminescent devices according to the invention are characterized, inter alia, by improved efficiency and/or operating voltage and by a higher lifetime compared to the prior art. The electronic device of the present invention, especially the organic electroluminescent device, is noteworthy for one or more of the following surprising advantages over the prior art: 1. preferably comprising formula (I) or described above and below Electronic devices of structures/compounds (as emitters) of embodiments, especially organic electroluminescent devices, have very narrow luminescent bands with very low FWHM (full width half maximum) values and lead to particularly pure color emission, which is recognizable by a low CIE y value. It is particularly surprising here to provide both blue emitters with low FWHM values and emitters with low FWHM values which emit light in the green, yellow or red region of the color spectrum. 2. An electronic device comprising a structure/compound of the formula (I) or a preferred embodiment described above and below (especially as a luminescent body, as a hole-conducting material and/or as an electron-transporting material), especially It has a very good lifetime for organic electroluminescent devices. In this context, these compounds lead in particular to low roll-off, ie the device has a small drop in power efficiency at high luminous intensities. 3. An electronic device comprising a structure/compound (as a luminescent body and/or as an electron transport material) of the formula (I) or a preferred embodiment described above and below, especially an organic electroluminescent device having Excellent efficiency. In this context, when the structures/compounds of the formula (I) of the present invention or the preferred embodiments described above and below are used in electronic devices, they result in low operating voltages. 4. The structures/compounds of formula (I) or the preferred embodiments described above and below in the present invention exhibit very high stability and lifetime. 5. The structure/compound of the formula (I) or the preferred embodiments described above and below may avoid the formation of optical loss channels in electronic devices, especially in organic electroluminescent devices. These devices are thus characterized by a high PL efficiency and thus a high EL efficiency of the emitter, and an excellent energy transfer of the host to the dopant. Exciton energy is usually transferred from the matrix or host in the emitting layer to the emitter via the so-called Dexter transfer or via the Förster transfer. The Foster energy transfer (FRET) from the host or substrate to the emitter of the invention is particularly preferred here because it is particularly efficient, which leads to particularly good performance data (eg efficiency, voltage and lifetime) of electronic devices. It was found that energy is transferred from the host or substrate to the compounds of the invention preferably via Forster transfer. 6. The structure/compound of the formula (I) or the preferred embodiments described above and below has excellent glass film-forming properties. 7. The structures/compounds of formula (I) or the preferred embodiments described above and below form very good films from solutions and exhibit excellent solubility. These aforementioned advantages are not accompanied by unduly high degradation of other electronic properties. It should be pointed out that variations of the embodiments described in the present invention are covered by the scope of the present invention. Unless expressly excluded, any feature disclosed herein may be exchanged for alternative features serving the same purpose or an equivalent or similar purpose. Accordingly, any feature disclosed herein is to be considered an example of a generic series or an equivalent or similar feature, unless otherwise stated. All features of the invention can be combined with each other in any way, unless certain features and/or steps are mutually exclusive. This is especially true of the preferred features of the present invention. Likewise, features in optional combinations may be used alone (and not in combination). It should also be pointed out that many of the features and especially those which are preferred embodiments of the invention are to be considered novel in themselves and not merely as some embodiments of the invention. Independent protection may be sought for such features in addition to or in lieu of any presently claimed invention. The technical guidance disclosed in the present invention can be summarized and combined with other examples. The invention is illustrated in more detail by the following examples without any intention to limit the invention thereby. A person skilled in the art is able to use the information given to carry out the invention within the scope of the disclosure without using innovative skills to prepare other compounds of the invention and to use these compounds in electronic devices or utilize the methods of the invention .

實施例 隨後的合成係在保護性氣體氣氛下於無水溶劑中進行，除非另有其他聲明。金屬錯合物係在避光或在黃光下另外處置。溶劑及試劑可購自例如Sigma-ALDRICH或ABCR。在方括號中的各個數字或對個別化合物所引用之數字係與自文獻已知的化合物之CAS編號有關。在化合物可具有多種鏡像異構物、非鏡像異構物或互變異構物形式的例子中，以代表性方式顯示一種形式。 自文獻已知的合成組元LS：

Figure 02_image351
合成組元S之合成： 自文獻已知的反應物： 1)   1,2-二氫吲唑-3-酮：
Figure 02_image353
2) 醯氯：
Figure 02_image355
Figure 02_image357
實施例S1：
Figure 02_image359
根據Z. Wang等人之Chin. J. Chem., 29, 2769, 2011之程序。 將21.3 g(100 mmol)之7-溴-1,2-二氫-3H-吲唑-3-酮[887578-57-6]、39.1 g(130 mmol)之2-氯-6-碘苯甲醯氯[1261850-84-3]、97.8 g(300 mmol)之無水碳酸銫、3.6 g (20 mmol)之1,10-啡啉、1.9 g(10 mmol)之碘化銅、200 g之玻璃珠(直徑3 mm)與800 ml之甲苯的混合物在100℃下攪拌16 h(TLC監測完全轉化成7-溴-1,2-二氫-3H-吲唑-3-酮)。將混合物靜置冷卻至80℃且以熱甲苯漿液的形式通過矽藻土床過濾，且將過濾物在減壓下濃縮至乾燥。將殘餘物溶解在500 ml之二氯甲烷(DCM)中且施加至約400 g之矽膠，將矽膠以DCM漿液(800 g)形式裝填至矽膠管柱中且使用DCM溶析反側-二苯并畢蔓(dibenzobimane)區域異構物。然後將所欲同側-二苯并畢蔓區域異構物以8:2之DCM：甲基三級丁醚(MTBE)溶析，且將其自乙腈再結晶一次。產率：9.5 g (27 mmol)，27%。純度：以 1H NMR為97%。 可類似地製備下列的化合物：
Figure 02_image361
Figure 02_image363
Figure 02_image365
Figure 02_image367
Figure 02_image369
Figure 02_image371
Figure 02_image373
實施例S50：
Figure 02_image375
將37.4 g(210 mmol)之N-溴琥珀醯亞胺在暗處於室溫下分批添加至500 ml之DCM中的23.6 g(100 mmol)之同側-二苯并畢蔓[125213-40-3]LS1的充分攪拌溶液中，且接著將混合物再攪拌12 h。將反應混合物以每次300 ml之水清洗三次及以300 ml之氯化鈉飽和溶液清洗一次且經硫酸鈉乾燥。濾出乾燥劑，添加100 ml之甲醇，將過濾物在旋轉蒸發器上濃縮至約80 ml體積，將結晶產物以抽吸濾出且以少量甲醇清洗兩次。產率：26.7 g(68 mmol)，68%。純度：以 1H NMR為97%。 可類似地製備下列化合物：
Figure 02_image377
實施例Int-D1：
Figure 02_image379
將26.0 g(33.7 mmol)之Int-A1[2171483-83-1]溶解在600 ml之二氯甲烷中。在暗處添加一滴HBr(33%，水性)，分批添加7.2 g(44.0 mmol)之N-溴琥珀醯亞胺且將混合物在室溫下攪拌48 h。在48 h後，添加200 ml之亞硫酸氫鈉飽和水溶液且將混合物再攪拌1 h。然後將兩相分開，將有機相以每次200 ml之水清洗三次且接著在減壓下濃縮。將殘餘物與300 ml之正庚烷摻合且在回流下加熱1小時。在混合物已冷卻後，將無色固體濾出，以每次50 ml之正庚烷清洗兩次且在減壓下乾燥。產率：25.3 g(32 mmol)，97%。純度：以HPLC為約98%。
Figure 02_image381
將1100 ml之THF及550 ml之水添加至28.0 g(35.5 mmol)之Int-B1、33.6 g(35.5 mmol)之[2171483-74-0]及9.8 g(71 mmol)之碳酸鉀中。然後添加373 mg(1.4 mmol)之三苯膦及325 mg(0.4 mmol)之三(二亞苯甲基丙酮)二鈀且將混合物在回流下加熱16 h。將500 ml之水及500 ml之甲苯添加至冷卻之反應混合物中；將相分開。將水相以200 ml之甲苯萃取兩次且將合併的有機相以500 ml之水清洗一次。將有機相通過氧化鋁過濾且接著濃縮至乾燥。將產物以自1:10之甲苯/正庚烷重複結晶純化且獲得固體形式。產率：41.0 g(28.8 mmol)，81%。純度：以HPLC為約98%。
Figure 02_image383
將750 ml之二㗁烷添加至25.3 g(18.7 mmol)之Int-C1、8.6 g(33.7 mmol)之雙(頻哪醇)二硼烷(bis(pinacolato) diborane)、5.5 g(56 mmol)之乙酸鉀及830 mg(1.1 mmol)之反-二氯雙(三環己膦)鈀(II)中，且將混合物在回流下加熱48 h。然後將1000 ml之甲苯及1000 ml之水添加至反應混合物中且將相分開。將水相以每次200 ml之甲苯萃取兩次且將合併的有機相以每次500 ml之水清洗兩次，通過氧化鋁過濾且濃縮至乾燥。將殘餘物與熱乙醇攪拌以進行萃取。產率：16.0 g(11.1 mmol)，60%。純度：以HPLC為約99%。 本發明化合物V之製備： 實施例V1
Figure 02_image385
將27.1 g(100 mmol)之S39、39.6g(110 mmol)之9,9'-螺二茀-2-硼酸[236389-21-2]、21.2 g(100 mmol)之磷酸三鉀、1.64 g(4 mmol)之S-Phos、499 mg(2 mmol)之乙酸鈀(II)、300 ml之甲苯、100 ml之二㗁烷與300 ml之水的混合物在70℃下攪拌12 h(有可能替代地使用AmPhosPdCl 2[887919-35-9])。在冷卻後，將有機相移出且以每次300 ml之水清洗兩次及以300 ml之氯化鈉飽和溶液清洗一次。將有機相濃縮至乾燥，將殘餘物溶解在二氯甲烷(DCM)中且以DCM漿液形式通過矽膠床過濾，且將過濾物在旋轉蒸發器上濃縮，以甲醇連續置換以旋轉蒸發移除之DCM。將結晶產物以抽吸濾出，以每次50 ml之甲醇清洗兩次且在減壓下乾燥。以熱萃取結晶(溶劑混合物：1:3至3:1之DCM/乙腈)及分昇華實現進一步純化。產率：31.5 g(57 mmol)，57%。純度：以HPLC為約99.9%。 可類似地製備下列化合物：
Figure 02_image387
Figure 02_image389
Figure 02_image391
Figure 02_image393
Figure 02_image395
Figure 02_image397
Figure 02_image399
Figure 02_image401
Figure 02_image403
Figure 02_image405
Figure 02_image407
Figure 02_image409
Figure 02_image411
Figure 02_image413
Figure 02_image415
Figure 02_image417
Figure 02_image419
Figure 02_image421
Figure 02_image423
Figure 02_image425
Figure 02_image427
Figure 02_image429
Figure 02_image431
Figure 02_image433
Figure 02_image435
Figure 02_image437
Figure 02_image439
實施例V200： 步驟1：溴鈴木偶合
Figure 02_image441
將35.0 g(100 mmol)之S1、g(110 mmol)之1-二苯并呋喃基硼酸[162607-19-4]、10.6 g(100 mmol)之碳酸鈉、1.83 g(6 mmol)之三-鄰甲苯膦、225 mg(1 mmol)之乙酸鈀(II)、400 ml之甲苯、200 ml之二㗁烷與400 ml之水的混合物在回流下加熱24 h。在冷卻後，將有機相移出且以每次300 ml之水清洗兩次及以300 ml之氯化鈉飽和溶液清洗一次。將有機相濃縮至乾燥，將殘餘物溶解在二氯甲烷(DCM)中且以DCM漿液形式通過矽膠床過濾，且將過濾物在旋轉蒸發器上濃縮，以甲醇連續置換以旋轉蒸發移除之DCM。將結晶產物以抽吸濾出，以每次50 ml之甲醇清洗兩次且在減壓下乾燥。將粗製產物自乙腈再結晶。產率：30.3 g(69 mmol)，69%。純度：以 1H NMR為約98%。 步驟2：氯鈴木偶合
Figure 02_image443
以類似於實施例V1的程序，使用3-(9H-咔唑-9-基)苯基硼酸[864377-33-3]。產率：30.3 g(47 mmol), 47%。純度：以 1H NMR為約99.9%。 可類似地製備下列化合物：
Figure 02_image445
Figure 02_image447
Figure 02_image449
Figure 02_image451
Figure 02_image453
Figure 02_image455
Figure 02_image457
Figure 02_image459
Figure 02_image461
Figure 02_image463
實施例V300：
Figure 02_image465
將13.6 g(50 mmol)之S4, 31.2 g(110 mmol)之5,7-二氫-7,7-二甲基茚并[2,1-b]咔唑[1257220-47-5]、14.4 g(150 mmol)之三級丁醇鈉、2.65 g(4 mmol)之rac-BINAP(有可能替代地使用S-Phos、X-Phos、三-三級丁膦)、674 mg(3 mmol)之乙酸鈀(II)、100 g之玻璃珠(直徑3 mm)與300 ml之甲苯的混合物在110℃下攪拌24 h。在混合物仍為熱的同時，將其以熱甲苯漿液形式以抽吸通過矽藻土床過濾，將過濾物在減壓下濃縮至乾燥且將固體在300 ml之熱甲醇中攪拌萃取。將固體以抽吸濾出，在混合物仍為溫熱的同時，以每次50 ml之甲醇清洗兩次且在減壓下乾燥。以熱萃取結晶(溶劑混合物：1:3至3:1之DCM/乙腈)及分昇華實現進一步純化。產率：20.1 g (25 mol)，50%。純度：以HPLC為約99.9%。 可類似地製備下列化合物：
Figure 02_image467
Figure 02_image469
Figure 02_image471
Figure 02_image473
實施例L1：
Figure 02_image475
將8.27 g(21 mmol)之S50、32.60 g (46 mmol)之OA1及4.5 g (42.4 mmol)之碳酸鈉懸浮在甲苯/乙醇/水(2:1:1)之600 ml混合物中且以氬氣脫氣。在添加613 mg(0.53 mmol)之肆(三苯膦)鈀(0)後，將混合物在110℃下攪拌。在六小時後，容許反應混合物冷卻至室溫且添加另外200 ml之甲苯。將有機相移出，以每次300 ml之水清洗兩次及以300 ml之氯化鈉飽和溶液清洗一次，經硫酸鈉乾燥且以甲苯漿液形式通過矽藻土床過濾。將過濾物濃縮至乾燥且將殘餘物溶解在300 ml之二氯甲烷中，添加200 ml之甲醇且將混合物在旋轉蒸發器上濃縮至約300 ml。將沉澱固體以抽吸濾出且以每次50 ml之甲醇清洗三次。將獲得的固體藉助於管柱層析術及自甲苯/正庚烷重複再結晶以進行純化，直到HPLC純度＞99.9%，且最終在10 -6毫巴及250℃下進行熱處理。產率：6.85 g(4.9 mmol)，24%。 可以類似的方式合成下列化合物：
Figure 02_image477
光致發光光譜(Photoluminescence spectra, PL光譜)之測量： 圖1顯示本發明化合物V53、V98和V99之PL光譜，其係以Hitachi F-4500 PL光譜儀在室溫下(約25℃)於約10 -5莫耳脫氣甲苯溶液中測量。 PL光譜具有非常窄的發光帶，具有低的FWHM值(＜0.18 eV)且導致特別純的色發光。 OLED組件之製造 1)經真空加工之裝置： 本發明之OLED及根據先前技術之OLED係以根據 WO 2004/058911之通用方法製造，該方法適用於在此所述之狀況(層厚度變化、所使用之材料)。 在隨後的實施例中呈現各種OLED的結果。將塗以厚度50 nm之結構化ITO (銦錫氧化物)的經潔淨之玻璃板(在Miele實驗室玻璃清洗機中以Merck Extran洗滌劑潔淨)以UV臭氧(來自UVP之PR-100 UV臭氧產生器)預處理25分鐘，且為了改進加工，在30分鐘內以20 nm之PEDOT：PSS (聚(3,4-伸乙二氧基噻吩)聚(苯乙烯磺酸酯)(以CLEVIOS™ P VP AI 4083自Heraeus Precious Metals GmbH Deutschland購得，自水溶液旋轉塗佈)塗佈，且接著在180℃下烘烤10分鐘。該等經塗佈之玻璃板形成欲施加至OLED之基板。 1a) 藍色和綠色螢光OLED組件-BF和GF： 將所有材料以熱氣相沉積法於真空室中施加。發光層(EML)在此總是由至少一種基質材料(主體材料)SMB(參見表1)及藉由共蒸發而以特定的體積比例添加至基質材料中的發光摻雜劑(摻雜劑，發光體)V所組成。以SMB：V (97：3%)的此形式給出之詳情在此意指材料SMB係以97%之體積比例存在於層中及摻雜劑V係以3%之體積比例存在於層中。本發明化合物V44、V45和V46類似地用作為發綠色螢光之組件的主體。電子傳輸層亦可類似地由兩種材料之混合物所組成；參見表1。用於製造OLED之材料顯示於表7中。 OLED係以標準方式特徵化。出於此目的，電致發光光譜、電流效率(以cd/A測量)、功率效率(以lm/W測量)及外部量子效率(EQE，以%測量)係自假設朗伯(Lambertian)發射特徵之電流-電壓-發光強度特徵(IUL特徵)以發光強度為函數計算，且亦測定壽命。電致發光光譜係在1000 cd/m²之發光強度下測定且使用該等光譜計算CIE 1931 x和y色座標及FWHM(在半高之全寬)。 OLED具有以下的層結構： 基板 電洞注入層1(HIL1)，由與5%之NDP-9(在市場上取自Novaled)摻雜之HTM1所組成，20 nm 電洞傳輸層1(HTL1)，由HTM1所組成，140 nm 電洞傳輸層2(HTL2)，由HTM2所組成，10 nm 發光層(EML)，參見表1 電子傳輸層(ETL2)，參見表1 電子傳輸層(ETL1)，參見表1 電子注入層(EIL)，由ETM2所組成，1 nm 陰極，由鋁所組成，100 nm
Figure 02_image479
Figure 02_image481
1b) 磷光OLED組件-BP、GP、RP： 在其他用途中，本發明化合物可用作為磷光OLED之發光層EML中的電子傳導主體材料eTMM及用作為HBL和ETL中的電子傳輸材料。 出於此目的，將所有材料以熱氣相沉積法於真空室中施加。發光層在此(EML)總是由至少一種或超過一種基質材料M (主體材料)及藉由共蒸發而以特定的體積比例添加至基質材料中的磷光摻雜劑Ir所組成。以M1：M2：Ir (55%：35%：10%)的此形式給出之詳情在此意指材料M1係以55%之體積比例，M2係以35%之體積比例及Ir係以10%之體積比例存在於層中。電子傳輸層亦可類似地由兩種材料之混合物所組成。OLED之真實結構可見於表3中。用於製造OLED之材料顯示於表7中。 OLED係以標準方式特徵化。出於此目的，電致發光光譜、電流效率(以cd/A測量)、功率效率(以lm/W測量)及外部量子效率(EQE，以%測量)係自假設朗伯發射特徵之電流-電壓-發光強度特徵(IUL特徵)以發光強度為函數計算，且亦測定壽命。電致發光光譜係在1000 cd/m²之發光強度下測定且使用該等光譜計算CIE 1931 x和y色座標。 OLED具有以下的層結構： 基板 電洞注入層1(HIL1)，由與5%之NDP-9(在市場上取自Novaled)摻雜之HTM1所組成，20 nm 電洞傳輸層1(HTL1)，由HTM1所組成，以170 nm用於藍色，以40 nm用於綠色/黃色，及以90 nm用於紅色組件 電洞傳輸層2(HTL2)，參見表3 發光層(EML)，參見表3 電子傳輸層(ETL2)，參見表3 電子傳輸層(ETL1)，參見表3 電子注入層(EIL)，由ETM2所組成，1 nm 陰極，由鋁所組成，100 nm
Figure 02_image483
Figure 02_image485
2) 經溶液加工之組件： 2a) 經溶液加工之磷光OLED組件-sol-GP和sol-RP： 本發明之銥錯合物亦可自溶液中加工且其中得到OLED，其與經真空加工之OLED相比而在加工技術方面更簡單得多，但仍具有良好的性質。此等組件之製造係基於聚合物發光二極體(PLED)之製造，其已於文獻中說明多次(例如在WO 2004/037887中)。結構係由下列所組成： 所使用之構造因此係如下： -     基板， -     ITO(50 nm)， -     電洞注入層(60 nm)， -     中間層(20 nm)，由HTL-S1所組成 -     發光層(60 nm)，參見表5 -     電洞阻擋層(10 nm)，由ETM-1所組成 -     電子傳輸層(40 nm)，由ETM-1/ETM-2(50:50)所組成 -     陰極(Al)(100 nm) 出於此目的，使用來自Technoprint(鈉鈣玻璃)之基板，將ITO結構(銦錫氧化物，透明的導電陽極)施加至基板。將基板在潔淨室中以DI水及洗滌劑(Deconex 15 PF)潔淨且接著以UV/臭氧電漿處理而活化。在此之後，同樣在潔淨室中以旋轉塗佈施加20 nm電洞注入層(來自Clevios™之PEDOT:PSS)。所需之旋轉速率係取決於稀釋程度及特定的旋轉塗佈機幾何形狀而定。為了移除層的殘餘水，將基板在空氣中於熱板上以180℃烘烤10分鐘。所使用之中間層適合於電洞傳輸；在此例子中，使用來自Merck之HTL-S1(WO2013156130)。固體含量為約5 g/l，以便藉助於旋轉塗佈而達成20 nm之層厚度。將中間層在惰性氣體氛圍中(在本例子中為氬氣)於熱板上以220℃烘烤30分鐘。中間層亦可替代地以一或多個層置換，該層僅必須滿足不因自溶液沉積EML之後續加工步驟而再浸出的條件。為了製造發光層，將三重態發光體Ir與基質材料一起溶解在甲苯或氯苯中。此等溶液之典型的固體含量係介於16與25 g/l之間，在此時裝置特有的60 nm層厚度係藉助於旋轉塗佈達成。經溶液加工之裝置含有由Ma：Mb：Ir(w%：x%：z%)所組成之發光層；參見表5。將發光層在惰性氣體氛圍中(在本例子中為氬氣)旋轉且在160℃下烘烤10分鐘。經氣相沉積之後者為電洞阻擋層及電子傳輸層(來自Lesker之氣相沉積系統或類似者，典型的氣相沉積壓力5×10 -6毫巴)。最後，以氣相沉積法施加氧化鋁(來自Aldrich之高純度金屬)之陰極。為了保護裝置免於空氣及大氣水分，最後將裝置封裝且接著特徵化。本文所引用之OLED實施例尚未優化。表5彙總所獲得的數據。
Figure 02_image487
2b) 經溶液加工之螢光OLED組件-sol-GP 本發明之螢光發光體L可同樣地自溶液加工且得到良好的性質。此等組件係與經溶液加工之磷光OLED組件-GP、RP的類似方式製造，進行如下所述之構造上的調整： -     基板， -     ITO(50 nm)， -     電洞注入層(20 nm)， -     中間層(20 nm)，由HTL-S1所組成 -     發光層(40 nm)，由螢光發光體L及基質MS所組成 -     電洞阻擋層(10 nm)，由ETM-1所組成 -     電子傳輸層(40 nm)，由ETM-1/ETM-2(50:50)所組成 -     陰極(Al)(100 nm)。 為了製造發光層，將螢光發光體L(5重量%)與基質材料MS(95重量%)一起溶解在甲苯或氯苯中。此等溶液之典型的固體含量為14 g/l，在此時裝置特有的40 nm層厚度係藉助於旋轉塗佈達成。將發光層在惰性氣體氛圍中(在本例子中為氬氣)旋轉且在160℃下烘烤10分鐘。表6彙總所獲得的數據。
Figure 02_image489
Figure 02_image491
Figure 02_image493
Figure 02_image495
Figure 02_image497
在關於本發明之材料的表1、3、5和6中所示之縮寫，例如L1、L2、L3、L4、V1、V4、V5、V6、V9、V12、V22、V24、V32、V35、V44、V45、V54、V57、V64、V65、V67、V83、V94、V200、V213和V307等係與上文合成實施例中詳細敘述之化合物有關。 EXAMPLES The subsequent syntheses were carried out in anhydrous solvents under a protective gas atmosphere, unless otherwise stated. Metal complexes are protected from light or otherwise handled under yellow light. Solvents and reagents are commercially available from, eg, Sigma-ALDRICH or ABCR. Each number in square brackets or referenced to an individual compound relates to the CAS number of the compound known from the literature. In instances where a compound may have multiple enantiomer, diastereomeric or tautomeric forms, one form is shown in a representative manner. Synthetic component LS known from the literature:
Figure 02_image351
Synthesis of synthetic component S: Reactants known from literature: 1) 1,2-dihydroindazol-3-one:
Figure 02_image353
2) Acyl chloride:
Figure 02_image355
Figure 02_image357
Example S1:
Figure 02_image359
According to the procedure of Chin. J. Chem., 29, 2769, 2011 by Z. Wang et al. 21.3 g (100 mmol) of 7-bromo-1,2-dihydro-3H-indazol-3-one [887578-57-6], 39.1 g (130 mmol) of 2-chloro-6-iodobenzene Formyl chloride [1261850-84-3], 97.8 g (300 mmol) of anhydrous cesium carbonate, 3.6 g (20 mmol) of 1,10-phenanthroline, 1.9 g (10 mmol) of copper iodide, 200 g of A mixture of glass beads (3 mm in diameter) and 800 ml of toluene was stirred at 100° C. for 16 h (complete conversion to 7-bromo-1,2-dihydro-3H-indazol-3-one monitored by TLC). The mixture was left to cool to 80 °C and filtered through a bed of celite as a hot toluene slurry, and the filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in 500 ml of dichloromethane (DCM) and applied to about 400 g of silica gel, the silica gel was packed into a silica gel column as a DCM slurry (800 g) and trans-biphenyl was eluted using DCM And Bi Man (dibenzobimane) regioisomers. The desired ipso-dibenzobeeman regioisomer was then eluted in 8:2 DCM:methyl tertiary butyl ether (MTBE) and recrystallized once from acetonitrile. Yield: 9.5 g (27 mmol), 27%. Purity: 97% by 1 H NMR. The following compounds can be prepared analogously:
Figure 02_image361
Figure 02_image363
Figure 02_image365
Figure 02_image367
Figure 02_image369
Figure 02_image371
Figure 02_image373
Embodiment S50:
Figure 02_image375
37.4 g (210 mmol) of N-bromosuccinimide was added portionwise to 23.6 g (100 mmol) of ipsilateral-dibenzobiman[125213-40 in 500 ml of DCM at room temperature in the dark. -3] in a well-stirred solution of LS1, and then the mixture was stirred for another 12 h. The reaction mixture was washed three times with 300 ml of water and once with 300 ml of a saturated sodium chloride solution and dried over sodium sulfate. The desiccant was filtered off, 100 ml of methanol was added, the filtrate was concentrated on a rotary evaporator to a volume of about 80 ml, the crystalline product was filtered off with suction and washed twice with a small amount of methanol. Yield: 26.7 g (68 mmol), 68%. Purity: 97% by 1 H NMR. The following compounds can be prepared analogously:
Figure 02_image377
Example Int-D1:
Figure 02_image379
26.0 g (33.7 mmol) of Int-A1 [2171483-83-1] were dissolved in 600 ml of dichloromethane. One drop of HBr (33%, aq) was added in the dark, 7.2 g (44.0 mmol) of N-bromosuccinimide were added portionwise and the mixture was stirred at room temperature for 48 h. After 48 h, 200 ml of saturated aqueous sodium bisulfite were added and the mixture was stirred for a further 1 h. The two phases are then separated, the organic phase is washed three times with 200 ml of water each time and then concentrated under reduced pressure. The residue was admixed with 300 ml of n-heptane and heated at reflux for 1 hour. After the mixture had cooled, the colorless solid was filtered off, washed twice with 50 ml of n-heptane each and dried under reduced pressure. Yield: 25.3 g (32 mmol), 97%. Purity: about 98% by HPLC.
Figure 02_image381
1100 ml of THF and 550 ml of water were added to 28.0 g (35.5 mmol) of Int-B1, 33.6 g (35.5 mmol) of [2171483-74-0] and 9.8 g (71 mmol) of potassium carbonate. Then 373 mg (1.4 mmol) of triphenylphosphine and 325 mg (0.4 mmol) of tris(dibenzylideneacetone)dipalladium were added and the mixture was heated at reflux for 16 h. 500 ml of water and 500 ml of toluene were added to the cooled reaction mixture; the phases were separated. The aqueous phase was extracted twice with 200 ml of toluene and the combined organic phases were washed once with 500 ml of water. The organic phase was filtered through alumina and then concentrated to dryness. The product was purified by repeated crystallization from toluene/n-heptane 1:10 and obtained in solid form. Yield: 41.0 g (28.8 mmol), 81%. Purity: about 98% by HPLC.
Figure 02_image383
750 ml of dioxane was added to 25.3 g (18.7 mmol) of Int-Cl, 8.6 g (33.7 mmol) of bis(pinacolato) diborane, 5.5 g (56 mmol) Potassium acetate and 830 mg (1.1 mmol) of trans-dichlorobis(tricyclohexylphosphine)palladium(II), and the mixture was heated under reflux for 48 h. Then 1000 ml of toluene and 1000 ml of water were added to the reaction mixture and the phases were separated. The aqueous phase was extracted twice with 200 ml each of toluene and the combined organic phases were washed twice with 500 ml each of water, filtered through alumina and concentrated to dryness. The residue was stirred with hot ethanol for extraction. Yield: 16.0 g (11.1 mmol), 60%. Purity: about 99% by HPLC. Preparation of Compound V of the present invention: Example V1
Figure 02_image385
27.1 g (100 mmol) of S39, 39.6 g (110 mmol) of 9,9'-spirobioxane-2-boronic acid [236389-21-2], 21.2 g (100 mmol) of tripotassium phosphate, 1.64 g (4 mmol) of S-Phos, 499 mg (2 mmol) of palladium (II) acetate, 300 ml of toluene, 100 ml of dioxane and 300 ml of water were stirred at 70°C for 12 h (possibly AmPhosPdCl2 [887919-35-9]) was used instead. After cooling, the organic phase was removed and washed twice with 300 ml of water and once with 300 ml of a saturated sodium chloride solution. The organic phase was concentrated to dryness, the residue was dissolved in dichloromethane (DCM) and filtered through a bed of silica gel as a DCM slurry, and the filtrate was concentrated on a rotary evaporator and removed by rotary evaporation with successive displacements of methanol. DCM. The crystalline product was filtered off with suction, washed twice with 50 ml of methanol each time and dried under reduced pressure. Further purification was achieved by hot extractive crystallization (solvent mixture: DCM/acetonitrile from 1:3 to 3:1) and fractional sublimation. Yield: 31.5 g (57 mmol), 57%. Purity: about 99.9% by HPLC. The following compounds can be prepared analogously:
Figure 02_image387
Figure 02_image389
Figure 02_image391
Figure 02_image393
Figure 02_image395
Figure 02_image397
Figure 02_image399
Figure 02_image401
Figure 02_image403
Figure 02_image405
Figure 02_image407
Figure 02_image409
Figure 02_image411
Figure 02_image413
Figure 02_image415
Figure 02_image417
Figure 02_image419
Figure 02_image421
Figure 02_image423
Figure 02_image425
Figure 02_image427
Figure 02_image429
Figure 02_image431
Figure 02_image433
Figure 02_image435
Figure 02_image437
Figure 02_image439
Example V200: Step 1: Bromo-Suzuki Coupling
Figure 02_image441
Add 35.0 g (100 mmol) of S1, g (110 mmol) of 1-dibenzofurylboronic acid [162607-19-4], 10.6 g (100 mmol) of sodium carbonate, 1.83 g (6 mmol) of Tris - A mixture of o-tolylphosphine, 225 mg (1 mmol) of palladium(II) acetate, 400 ml of toluene, 200 ml of dioxane and 400 ml of water was heated under reflux for 24 h. After cooling, the organic phase was removed and washed twice with 300 ml of water and once with 300 ml of a saturated sodium chloride solution. The organic phase was concentrated to dryness, the residue was dissolved in dichloromethane (DCM) and filtered through a bed of silica gel as a DCM slurry, and the filtrate was concentrated on a rotary evaporator and removed by rotary evaporation with successive displacements of methanol. DCM. The crystalline product was filtered off with suction, washed twice with 50 ml of methanol each time and dried under reduced pressure. The crude product was recrystallized from acetonitrile. Yield: 30.3 g (69 mmol), 69%. Purity: about 98% by 1 H NMR. Step 2: Chlorine Suzuki Coupling
Figure 02_image443
In a procedure analogous to Example V1, 3-(9H-carbazol-9-yl)phenylboronic acid [864377-33-3] was used. Yield: 30.3 g (47 mmol), 47%. Purity: about 99.9% by 1 H NMR. The following compounds can be prepared analogously:
Figure 02_image445
Figure 02_image447
Figure 02_image449
Figure 02_image451
Figure 02_image453
Figure 02_image455
Figure 02_image457
Figure 02_image459
Figure 02_image461
Figure 02_image463
Example V300:
Figure 02_image465
13.6 g (50 mmol) of S4, 31.2 g (110 mmol) of 5,7-dihydro-7,7-dimethylindeno[2,1-b]carbazole[1257220-47-5], 14.4 g (150 mmol) of sodium tertiary butoxide, 2.65 g (4 mmol) of rac-BINAP (it is possible to use S-Phos, X-Phos, tri-tertiary butylphosphine instead), 674 mg (3 mmol ), a mixture of palladium(II) acetate, 100 g of glass beads (3 mm in diameter) and 300 ml of toluene was stirred at 110°C for 24 h. While the mixture was still hot, it was filtered as a hot toluene slurry with suction through a bed of celite, the filtrate was concentrated to dryness under reduced pressure and the solid extracted with stirring in 300 ml of hot methanol. The solid was filtered off with suction, washed twice with 50 ml each of methanol and dried under reduced pressure while the mixture was still warm. Further purification was achieved by hot extractive crystallization (solvent mixture: DCM/acetonitrile from 1:3 to 3:1) and fractional sublimation. Yield: 20.1 g (25 mol), 50%. Purity: about 99.9% by HPLC. The following compounds can be prepared analogously:
Figure 02_image467
Figure 02_image469
Figure 02_image471
Figure 02_image473
Example L1:
Figure 02_image475
8.27 g (21 mmol) of S50, 32.60 g (46 mmol) of OA1 and 4.5 g (42.4 mmol) of sodium carbonate were suspended in a 600 ml mixture of toluene/ethanol/water (2:1:1) and heated with argon Degassing. After addition of 613 mg (0.53 mmol) of tetrakis(triphenylphosphine)palladium(0), the mixture was stirred at 110°C. After six hours, the reaction mixture was allowed to cool to room temperature and an additional 200 ml of toluene was added. The organic phase was removed, washed twice with 300 ml of water and once with 300 ml of saturated sodium chloride solution, dried over sodium sulfate and filtered through a bed of Celite as a toluene slurry. The filtrate was concentrated to dryness and the residue was dissolved in 300 ml of dichloromethane, 200 ml of methanol were added and the mixture was concentrated to about 300 ml on a rotary evaporator. The precipitated solid was filtered off with suction and washed three times with 50 ml of methanol each time. The solid obtained was purified by means of column chromatography and repeated recrystallization from toluene/n-heptane until HPLC purity >99.9% and finally heat treated at 10 −6 mbar and 250° C. Yield: 6.85 g (4.9 mmol), 24%. The following compounds can be synthesized in a similar manner:
Figure 02_image477
Measurement of photoluminescence spectrum (Photoluminescence spectrum, PL spectrum): Fig. 1 shows the PL spectrum of compounds V53, V98 and V99 of the present invention, which is at room temperature (about 25°C) at about 10 with a Hitachi F-4500 PL spectrometer -5 molar degassed toluene solution. The PL spectrum has very narrow luminescence bands with low FWHM values (<0.18 eV) and results in particularly pure color luminescence. Production of OLED Components 1) Vacuum-processed device: OLEDs according to the invention and OLEDs according to the prior art are produced with the general method according to WO 2004/058911, which is suitable for the conditions described here (layer thickness variations, all materials used). Results for various OLEDs are presented in the examples that follow. Cleaned glass plates (cleaned with Merck Extran detergent in a Miele laboratory glass washer) coated with structured ITO (Indium Tin Oxide) with a thickness of 50 nm were treated with UV ozone (PR-100 UV Ozone from UVP generator) for 25 minutes, and to improve processing, within 30 minutes with 20 nm of PEDOT:PSS (poly(3,4-ethylenedioxythiophene) poly(styrene sulfonate) (as CLEVIOS™ P VP AI 4083 was purchased from Heraeus Precious Metals GmbH Deutschland, spin-coated from an aqueous solution) and then baked at 180° C. for 10 minutes. The coated glass plates formed the substrate to be applied to the OLED. 1a ) Blue and Green Fluorescent OLED Components - BF and GF: All materials were applied by thermal vapor deposition in a vacuum chamber. The emitting layer (EML) here always consists of at least one matrix material (host material) SMB (see Table 1) and an emitting dopant (dopant, Luminous body) composed of V. The details given in this form SMB:V (97:3%) mean here that the material SMB is present in the layer in a volume fraction of 97% and the dopant V is present in the layer in a volume fraction of 3% . Compounds V44, V45 and V46 according to the invention were similarly used as hosts for green fluorescent components. The electron transport layer can similarly consist of a mixture of the two materials; see Table 1. The materials used to make OLEDs are shown in Table 7. OLEDs were characterized in a standard manner. For this purpose, the electroluminescence spectra, current efficiency (measured in cd/A), power efficiency (measured in lm/W), and external quantum efficiency (EQE, measured in %) were derived from assuming Lambertian emission characteristics The current-voltage-luminous intensity characteristic (IUL characteristic) is calculated as a function of the luminous intensity, and the lifetime is also determined. Electroluminescence spectra were measured at a luminous intensity of 1000 cd/m² and the CIE 1931 x and y color coordinates and FWHM (full width at half maximum) were calculated using these spectra. The OLED has the following layer structure: Substrate hole injection layer 1 (HIL1) consisting of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm hole transport layer 1 (HTL1) , composed of HTM1, 140 nm hole transport layer 2 (HTL2), composed of HTM2, 10 nm light-emitting layer (EML), see Table 1 Electron Transport Layer (ETL2), see Table 1 Electron Transport Layer (ETL1), See Table 1 Electron Injection Layer (EIL), composed of ETM2, 1 nm Cathode, composed of Aluminum, 100 nm
Figure 02_image479
Figure 02_image481
1b) Phosphorescent OLED components - BP, GP, RP: Among other uses, the compounds of the present invention can be used as electron-conducting host material eTMM in the emitting layer EML of phosphorescent OLED and as electron-transporting material in HBL and ETL. For this purpose, all materials were applied by thermal vapor deposition in a vacuum chamber. The emitting layer (EML) here always consists of at least one or more than one matrix material M (host material) and the phosphorescent dopant Ir added to the matrix material in specific volume proportions by co-evaporation. Details given in the form of M1:M2:Ir (55%:35%:10%) mean here that the material M1 is in a volume proportion of 55%, M2 is in a volume proportion of 35% and Ir is in a volume proportion of 10%. The volume fraction of % is present in the layer. The electron transport layer can similarly consist of a mixture of the two materials. The actual structure of the OLED can be seen in Table 3. The materials used to make OLEDs are shown in Table 7. OLEDs were characterized in a standard manner. For this purpose, the electroluminescence spectrum, current efficiency (measured in cd/A), power efficiency (measured in lm/W) and external quantum efficiency (EQE, measured in %) were obtained from the current- The voltage-luminous intensity characteristic (IUL characteristic) is calculated as a function of the luminous intensity and the lifetime is also determined. Electroluminescence spectra were measured at a luminous intensity of 1000 cd/m² and the CIE 1931 x and y color coordinates were calculated using these spectra. The OLED has the following layer structure: Substrate hole injection layer 1 (HIL1) consisting of HTM1 doped with 5% NDP-9 (commercially available from Novaled), 20 nm hole transport layer 1 (HTL1) , consisting of HTM1 at 170 nm for blue, 40 nm for green/yellow and 90 nm for red Components Hole Transport Layer 2 (HTL2), see Table 3 Emissive Layer (EML), see Table 3 Electron Transport Layer (ETL2), see Table 3 Electron Transport Layer (ETL1), see Table 3 Electron Injection Layer (EIL), composed of ETM2, 1 nm Cathode, composed of Aluminum, 100 nm
Figure 02_image483
Figure 02_image485
2) Solution Processed Components: 2a) Solution Processed Phosphorescent OLED Components - sol-GP and sol-RP: The iridium complexes according to the invention can also be processed from solution and OLEDs are obtained therein, which in combination with vacuum processed OLEDs are much simpler in terms of processing technology, but still have good properties. The manufacture of these components is based on the manufacture of polymer light emitting diodes (PLEDs), which has been described several times in the literature (for example in WO 2004/037887). The structure is composed of the following: The structure used is therefore as follows: - substrate, - ITO (50 nm), - hole injection layer (60 nm), - intermediate layer (20 nm), consisting of HTL-S1 - Emissive layer (60 nm), see Table 5 - Hole blocking layer (10 nm), composed of ETM-1 - Electron transport layer (40 nm), composed of ETM-1/ETM-2 (50:50) - Cathode (Al) (100 nm) For this purpose, a substrate from Technoprint (soda lime glass) was used, to which an ITO structure (indium tin oxide, transparent conductive anode) was applied. The substrates were cleaned in a clean room with DI water and detergent (Deconex 15 PF) and then activated with UV/ozone plasma treatment. After this, a 20 nm hole injection layer (PEDOT:PSS from Clevios™) was applied by spin coating, also in a clean room. The required spin rate will depend on the degree of dilution and the particular spin coater geometry. To remove residual water of the layer, the substrate was baked in air on a hot plate at 180° C. for 10 minutes. The interlayer used was suitable for hole transport; in this example HTL-S1 from Merck (WO2013156130) was used. The solids content was about 5 g/l in order to achieve a layer thickness of 20 nm by means of spin coating. The intermediate layer was baked on a hot plate at 220° C. for 30 minutes in an inert gas atmosphere (argon in this example). The intermediate layer may alternatively also be replaced by one or more layers which only have to fulfill the condition of not being releached by subsequent processing steps of the deposited EML from solution. To produce the emitting layer, the triplet emitter Ir is dissolved together with the matrix material in toluene or chlorobenzene. The typical solids content of these solutions is between 16 and 25 g/l, at which point the device-specific layer thickness of 60 nm is achieved by means of spin coating. The solution-processed device contained an emissive layer composed of Ma:Mb:Ir (w%:x%:z%); see Table 5. The light-emitting layer was rotated and baked at 160° C. for 10 minutes in an inert gas atmosphere (argon in this example). The latter are the hole blocking layer and the electron transport layer after vapor deposition (vapor deposition system from Lesker or similar, typical vapor deposition pressure 5×10 −6 mbar). Finally, a cathode of aluminum oxide (a high-purity metal from Aldrich) was applied by vapor deposition. To protect the device from air and atmospheric moisture, the device is finally packaged and then characterized. The OLED embodiments cited herein have not been optimized. Table 5 summarizes the data obtained.
Figure 02_image487
2b) Solution Processed Fluorescent OLED Component-sol-GP The fluorescent emitter L of the present invention can also be processed from solution and obtain good properties. These components were fabricated in a similar manner to solution processed phosphorescent OLED components - GP, RP, with the following structural adjustments: - substrate, - ITO (50 nm), - hole injection layer (20 nm) , - intermediate layer (20 nm), composed of HTL-S1 - light-emitting layer (40 nm), composed of fluorescent emitter L and matrix MS - hole blocking layer (10 nm), composed of ETM-1 - Electron transport layer (40 nm), composed of ETM-1/ETM-2 (50:50) - Cathode (Al) (100 nm). To produce the emitting layer, the phosphor L (5% by weight) is dissolved together with the matrix material MS (95% by weight) in toluene or chlorobenzene. A typical solids content of these solutions is 14 g/l, at which point a device-specific layer thickness of 40 nm is achieved by means of spin coating. The light-emitting layer was rotated and baked at 160° C. for 10 minutes in an inert gas atmosphere (argon in this example). Table 6 summarizes the data obtained.
Figure 02_image489
Figure 02_image491
Figure 02_image493
Figure 02_image495
Figure 02_image497
The abbreviations shown in Tables 1, 3, 5 and 6 for materials of the invention, such as L1, L2, L3, L4, V1, V4, V5, V6, V9, V12, V22, V24, V32, V35, V44, V45, V54, V57, V64, V65, V67, V83, V94, V200, V213 and V307 are related to the compounds described in detail in the above synthesis examples.

[圖1]顯示本發明化合物V53、V98和V99之PL光譜，其係以Hitachi F-4500 PL光譜儀在室溫下(約25℃)於約10 -5莫耳脫氣甲苯溶液中測量。 [ Fig. 1 ] shows the PL spectra of compounds V53, V98 and V99 of the present invention, which were measured in about 10 -5 molar degassed toluene solution at room temperature (about 25° C.) with a Hitachi F-4500 PL spectrometer.

Figure 111116223-A0101-11-0002-1
Figure 111116223-A0101-11-0002-1

Claims (18)

一種包括至少一種式(I)之結構之化合物，
Figure 03_image001
其中該環Ar a在各情況下為相同的或不同的且為具有5至60個芳族環原子且可經一或多個Ar或R a基團取代之芳族或雜芳族環系統，該環Ar b在各情況下為相同的或不同的且為具有5至60個芳族環原子且可經一或多個Ar或R b基團取代之芳族或雜芳族環系統； 且其中所使用之其他符號及標號係如下： W a、W b在各情況下為相同的或不同的且為O或S； Ar   在各情況下為相同的或不同的且為具有5至60個芳族環原子且可經一或多個R基團取代之芳族或雜芳族環系統；Ar基團在此可與至少一個Ar、R、R a、R b基團或另一基團形成環系統； R、R a、R b在各情況下為相同的或不同的且為H、D、OH、F、Cl、Br、I、CN、NO 2、N(Ar') 2、N(R 1) 2、C(=O)N(Ar') 2、C(=O)N(R 1) 2、C(Ar') 3、C(R 1) 3、Si(Ar') 3、Si(R 1) 3、B(Ar') 2、B(R 1) 2、C(=O)Ar'、C(=O)R 1、P(=O)(Ar') 2、P(=O)(R 1) 2、P(Ar') 2、P(R 1) 2、S(=O)Ar'、S(=O)R 1、S(=O) 2Ar'、S(=O) 2R 1、OSO 2Ar'、OSO 2R 1、具有1至40個碳原子的直鏈烷基、烷氧基或硫烷氧基、或具有2至40個碳原子的烯基或炔基、或具有3至20個碳原子的支鏈或環狀烷基、烷氧基或硫烷氧基，其中該等烷基、烷氧基、硫烷氧基、烯基或炔基可在各例子中經一或多個R 1基團取代，其中一或多個不相鄰的CH 2基團可經R 1C=CR 1、C≡C、Si(R 1) 2、C=O、C=S、C=Se、C=NR 1、-C(=O)O-、-C(=O)NR 1-、NR 1、P(=O)(R 1)、 -O-、-S-、SO或SO 2置換、或具有5至60個芳族環原子且可在各例子中經一或多個R 1基團取代之芳族或雜芳族環系統、或具有5至60個芳族環原子且可經一或多個R 1基團取代之芳氧基或雜芳氧基；或具有5至60個芳族環原子且可經一或多個R 1基團取代之雜芳硫基、或具有5至60個芳族環原子且可經一或多個R 1基團取代之二芳胺基、芳基雜芳胺基、二雜芳胺基、或具有5至60個芳族環原子及在烷基中的1至10個碳原子且可經一或多個R 1基團取代之芳烷基或雜芳基烷基；同時，兩個R、R a、R b基團亦可一起或與另一基團形成環系統； Ar'  在各情況下為相同的或不同的且為具有5至60個芳族環原子且可經一或多個R 1基團取代之芳族或雜芳族環系統；同時，與相同的碳原子、矽原子、氮原子、磷原子或硼原子鍵結之兩個Ar'基團亦有可能經由單鍵之橋或選自下列之橋接合在一起：B(R 1)、C(R 1) 2、Si(R 1) 2、C=O、C=NR 1、C=C(R 1) 2、O、S、S=O、SO 2、N(R 1)、P(R 1)和P(=O)R 1； R 1在各情況下為相同的或不同的且為H、D、F、Cl、Br、I、CN、NO 2、N(Ar") 2、N(R 2) 2、C(=O)Ar"、C(=O)R 2、P(=O)(Ar") 2、P(Ar") 2、B(Ar") 2、B(R 2) 2、C(Ar") 3、C(R 2) 3、Si(Ar") 3、Si(R 2) 3、具有1至40個碳原子的直鏈烷基、烷氧基或硫烷氧基、或具有3至40個碳原子的支鏈或環狀烷基、烷氧基或硫烷氧基、或具有2至40個碳原子的烯基，每一該等基團可經一或多個R 2基團取代，其中一或多個不相鄰的CH 2基團可經-R 2C=CR 2-、-C≡C-、Si(R 2) 2、C=O、C=S、C=Se、C=NR 2、-C(=O)O-、-C(=O)NR 2-、NR 2、P(=O)(R 2)、 -O-、-S-、SO或SO 2置換且其中一或多個氫原子可經D、F、Cl、Br、I、CN或NO 2置換、或具有5至60個芳族環原子的芳族或雜芳族環系統，每一該等基團可經一或多個R 2基團取代、或具有5至60個芳族環原子且可經一或多個R 2基團取代之芳氧基或雜芳氧基、或具有5至60個芳族環原子且可經一或多個R 2基團取代之芳烷基或雜芳烷基、或該等系統之組合；同時，二或更多個R 1基團可一起形成環系統；同時，一或多個R 1基團可與該化合物的其他部分形成環系統； Ar" 在各情況下為相同的或不同的且為具有5至30個芳族環原子且可經一或多個R 2基團取代之芳族或雜芳族環系統；同時，與相同的碳原子、矽原子、氮原子、磷原子或硼原子鍵結之兩個Ar"基團亦有可能經由單鍵之橋或選自下列之橋接合在一起：B(R 2)、C(R 2) 2、Si(R 2) 2、C=O、C=NR 2、C=C(R 2) 2、O、S、S=O、SO 2、N(R 2)、P(R 2)和P(=O)R 2； R 2在各情況下為相同的或不同的且選自由下列所組成之群組：H、D、F、CN、具有1至20個碳原子的脂族烴基、或具有5至30個芳族環原子的芳族或雜芳族環系統，且其中一或多個氫原子可經D、F、Cl、Br、I或CN置換，且其可經一或多個各具有1至4個碳原子的烷基取代；同時，二或更多個取代基R 2可一起形成環系統； 排除式(A)、(B)和(C)化合物之保護
Figure 03_image003
。 A compound comprising at least one structure of formula (I),
Figure 03_image001
wherein the rings Ar are in each case identical or different and are aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms which may be substituted by one or more Ar or Ra groups, The rings Ar b are in each case identical or different and are aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms which may be substituted by one or more Ar or R groups; and Wherein used other symbols and label system are as follows: W a , W b are the same or different in each case and are O or S; Ar are the same or different in each case and have 5 to 60 Aromatic or heteroaromatic ring systems which are aromatic ring atoms and which may be substituted by one or more R groups; the Ar group here may be combined with at least one Ar, R, R a , R b group or another group Forming a ring system; R, R a , R b are in each case the same or different and are H, D, OH, F, Cl, Br, I, CN, NO 2 , N(Ar′) 2 , N (R 1 ) 2 , C(=O)N(Ar') 2 , C(=O)N(R 1 ) 2 , C(Ar') 3 , C(R 1 ) 3 , Si(Ar') 3 , Si(R 1 ) 3 , B(Ar') 2 , B(R 1 ) 2 , C(=O)Ar', C(=O)R 1 , P(=O)(Ar') 2 , P (=O)(R 1 ) 2 , P(Ar') 2 , P(R 1 ) 2 , S(=O)Ar', S(=O)R 1 , S(=O) 2 Ar', S (=O) 2 R 1 , OSO 2 Ar', OSO 2 R 1 , linear alkyl, alkoxy or thioalkoxy having 1 to 40 carbon atoms, or alkenes having 2 to 40 carbon atoms or alkynyl, or branched or cyclic alkyl, alkoxy or thioalkoxy having 3 to 20 carbon atoms, wherein the alkyl, alkoxy, thioalkoxy, alkenyl or alkyne may be substituted in each instance by one or more R 1 groups, wherein one or more non-adjacent CH 2 groups may be substituted by R 1 C=CR 1 , C≡C, Si(R 1 ) 2 , C=O, C=S, C=Se, C=NR 1 , -C(=O)O-, -C(=O)NR 1 -, NR 1 , P(=O)(R 1 ), - O-, -S-, SO or SO replacement , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may in each case be substituted by one or more R groups, or Aryloxy or heteroaryloxy groups having 5 to 60 aromatic ring atoms which may be substituted by one or more R groups ; or having 5 to 60 aromatic ring atoms which may be substituted by one or more R groups A heteroarylthio group substituted by a group, or a diarylamino group, an arylheteroarylamine group, a diheteroarylamino group, which has 5 to 60 aromatic ring atoms and may be substituted by one or more R groups, or an aralkyl or heteroarylalkyl group having 5 to 60 aromatic ring atoms and 1 to 10 carbon atoms in the alkyl group and which may be substituted by one or more R groups ; at the same time, two R , R a , R b groups can also form a ring system together or with another group; Ar' are in each case the same or different and have 5 to 60 aromatic ring atoms and can be modified by one or more An aromatic or heteroaromatic ring system substituted by one R1 group; at the same time, two Ar' groups bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom are also possible via a single bond Bridges or bridges selected from the following: B(R 1 ), C(R 1 ) 2 , Si(R 1 ) 2 , C=O, C=NR 1 , C=C(R 1 ) 2 , O, S, S=O, SO 2 , N(R 1 ), P(R 1 ) and P(=O)R 1 ; R 1 are in each case the same or different and are H, D, F , Cl, Br, I, CN, NO 2 , N(Ar") 2 , N(R 2 ) 2 , C(=O)Ar", C(=O)R 2 , P(=O)(Ar" ) 2 , P(Ar") 2 , B(Ar") 2 , B(R 2 ) 2 , C(Ar") 3 , C(R 2 ) 3 , Si(Ar") 3 , Si(R 2 ) 3. Straight-chain alkyl, alkoxy or thioalkoxy with 1 to 40 carbon atoms, or branched or cyclic alkyl, alkoxy or thioalkoxy with 3 to 40 carbon atoms, Or an alkenyl group having 2 to 40 carbon atoms, each of which may be substituted by one or more R2 groups, wherein one or more non-adjacent CH2 groups may be replaced by -R2C = CR 2 -, -C≡C-, Si(R 2 ) 2 , C=O, C=S, C=Se, C=NR 2 , -C(=O)O-, -C(=O)NR 2 -, NR 2 , P(=O)(R 2 ), -O-, -S-, SO or SO 2 and one or more hydrogen atoms can be replaced by D, F, Cl, Br, I, CN or NO replacement, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more R groups, or having 5 to 60 aromatic ring systems Aryloxy or heteroaryloxy which is an aromatic ring atom and which may be substituted by one or more R groups, or aralkyl which has 5 to 60 aromatic ring atoms and which may be substituted by one or more R groups group or heteroarylalkyl group, or a combination of these systems; at the same time, two or more R1 groups can form a ring system together; at the same time, one or more R1 groups can form a ring system with other parts of the compound system; Ar" is in each case the same or different and is an aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms and which may be substituted by one or more R groups; meanwhile, with Two Ar" groups bonded to the same carbon atom, silicon atom, nitrogen atom, phosphorus atom or boron atom may also be bonded together via a bridge of a single bond or a bridge selected from the following: B(R 2 ), C (R 2 ) 2 , Si(R 2 ) 2 , C=O, C=NR 2 , C=C(R 2 ) 2 , O, S, S=O, SO 2 , N(R 2 ), P( R 2 ) and P(=O)R 2 ; R 2 are in each case the same or different and are selected from the group consisting of H, D, F, CN, C having 1 to 20 carbon atoms Aliphatic hydrocarbon group, or aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms, and wherein one or more hydrogen atoms can be replaced by D, F, Cl, Br, I or CN, and it can be Substituted by one or more alkyl groups each having 1 to 4 carbon atoms; at the same time, two or more substituents R 2 can form a ring system together; Excluding compounds of formula (A), (B) and (C) Protect
Figure 03_image003
. 根據請求項1之化合物，其包含至少一個式(II-1)至(II-42)之結構：
Figure 03_image005
Figure 03_image007
Figure 03_image009
Figure 03_image011
Figure 03_image013
Figure 03_image015
Figure 03_image017
Figure 03_image019
Figure 03_image021
Figure 03_image023
Figure 03_image025
Figure 03_image027
Figure 03_image029
Figure 03_image031
Figure 03_image033
Figure 03_image035
Figure 03_image037
Figure 03_image039
Figure 03_image041
Figure 03_image043
Figure 03_image045
Figure 03_image047
Figure 03_image049
Figure 03_image051
Figure 03_image053
Figure 03_image055
Figure 03_image057
Figure 03_image059
Figure 03_image061
Figure 03_image063
Figure 03_image065
Figure 03_image067
Figure 03_image069
Figure 03_image071
Figure 03_image073
Figure 03_image075
Figure 03_image077
Figure 03_image079
Figure 03_image081
Figure 03_image083
Figure 03_image085
Figure 03_image087
其中符號W a和W b具有以請求項1給出之定義，且其他符號係如下： Y a在各情況下為相同的或不同的且為N(Ar)、N(R a)、P(Ar)、P(R a)、P(=O)Ar、P(=O)R a、P(=S)Ar、P(=S)R a、B(Ar)、B(R a)、Al(Ar)、Al(R a)、Ga(Ar)、Ga(R a)、C=O、C(R a) 2、Si(R a) 2、Ge(R a) 2、C=NR a、C=NAr、C=C(R a) 2、C=C(R a)(Ar)、O、S、Se、S=O或SO 2，較佳為N(Ar)、N(R a)、B(Ar)、B(R a)、P(=O)R a、P(=O)Ar、C=O、C(R a) 2、C=C(R a) 2、C=C(R a)(Ar)、Si(R a) 2、O、S、Se、S=O或SO 2，更佳為N(Ar)、C(R a) 2、O或S，其中R a具有以請求項1詳述之定義； Y b在各情況下為相同的或不同的且為N(Ar)、N(R b)、P(Ar)、P(R b)、P(=O)Ar、P(=O)R b、P(=S)Ar、P(=S)R b、B(Ar)、B(R b)、Al(Ar)、Al(R a)、Ga(Ar)、Ga(R b)、C=O、C(R b) 2、Si(R b) 2、Ge(R b) 2、C=NR b、C=NAr、C=C(R b) 2、C=C(R b)(Ar)、O、S、Se、S=O或SO 2，較佳為N(Ar)、N(R b)、B(Ar)、B(R b)、P(=O)R b、P(=O)Ar、C=O、C(R b) 2、C=C(R b) 2、C=C(R b)(Ar)、Si(R b) 2、O、S、Se、S=O或SO 2，更佳為N(Ar)、C(R b) 2、O或S，其中R b具有以請求項1詳述之定義； Y 1、Y 2在各情況下為相同的或不同的且為N(Ar)、N(R)、P(Ar)、P(R)、P(=O)Ar、P(=O)R、P(=S)Ar、P(=S)R、B(Ar)、B(R)、Al(Ar)、Al(R)、Ga(Ar)、Ga(R)、C=O、C(R) 2、Si(R) 2、Ge(R) 2、C=NR、C=NAr、C=C(R) 2、C=C(R)(Ar)、O、S、Se、S=O或SO 2，較佳為N(Ar)、N(R)、B(Ar)、B(R)、P(=O)R、P(=O)Ar、C=O、C(R) 2、C=C(R) 2、C=C(R)(Ar)、Si(R) 2、O、S、Se、S=O或SO 2，更佳為N(Ar)、C(R) 2、O或S，其中R具有以請求項1詳述之定義； X    在各情況下為相同的或不同的且為N或CR，其先決條件為在一個環中的X基團不超過兩個為N，其中R具有以請求項1詳述之定義； X a在各情況下為相同的或不同的且為N或CR a，其先決條件為在一個環中的X a基團不超過兩個為N，其中R a具有以請求項1詳述之定義； X b在各情況下為相同的或不同的且為N或CR b，其先決條件為在一個環中的X b基團不超過兩個為N，其中R b具有以請求項1詳述之定義。 The compound according to claim 1, which comprises at least one structure of formulas (II-1) to (II-42):
Figure 03_image005
Figure 03_image007
Figure 03_image009
Figure 03_image011
Figure 03_image013
Figure 03_image015
Figure 03_image017
Figure 03_image019
Figure 03_image021
Figure 03_image023
Figure 03_image025
Figure 03_image027
Figure 03_image029
Figure 03_image031
Figure 03_image033
Figure 03_image035
Figure 03_image037
Figure 03_image039
Figure 03_image041
Figure 03_image043
Figure 03_image045
Figure 03_image047
Figure 03_image049
Figure 03_image051
Figure 03_image053
Figure 03_image055
Figure 03_image057
Figure 03_image059
Figure 03_image061
Figure 03_image063
Figure 03_image065
Figure 03_image067
Figure 03_image069
Figure 03_image071
Figure 03_image073
Figure 03_image075
Figure 03_image077
Figure 03_image079
Figure 03_image081
Figure 03_image083
Figure 03_image085
Figure 03_image087
where the symbols W a and W b have the definitions given in Claim 1, and the other symbols are as follows: Y a is in each case the same or different and is N(Ar), N(R a ), P( Ar), P(R a ), P(=O)Ar, P(=O)R a , P(=S)Ar, P(=S)R a , B(Ar), B(R a ), Al(Ar), Al(R a ), Ga(Ar), Ga(R a ), C=O, C(R a ) 2 , Si(R a ) 2 , Ge(R a ) 2 , C=NR a , C=NAr, C=C(R a ) 2 , C=C(R a )(Ar), O, S, Se, S=O or SO 2 , preferably N(Ar), N(R a ), B(Ar), B(R a ), P(=O)R a , P(=O)Ar, C=O, C(R a ) 2 , C=C(R a ) 2 , C =C(R a )(Ar), Si(R a ) 2 , O, S, Se, S=O or SO 2 , more preferably N(Ar), C(R a ) 2 , O or S, wherein R a has the definition specified in claim 1; Y b is in each case the same or different and is N(Ar), N(R b ), P(Ar), P(R b ), P( =O)Ar, P(=O)R b , P(=S)Ar, P(=S)R b , B(Ar), B(R b ), Al(Ar), Al(R a ), Ga(Ar), Ga(R b ), C=O, C(R b ) 2 , Si(R b ) 2 , Ge(R b ) 2 , C=NR b , C=NAr, C=C(R b ) 2 , C=C(R b )(Ar), O, S, Se, S=O or SO 2 , preferably N(Ar), N(R b ), B(Ar), B(R b ), P(=O)R b , P(=O)Ar, C=O, C(R b ) 2 , C=C(R b ) 2 , C=C(R b )(Ar), Si (R b ) 2 , O, S, Se, S=O or SO 2 , more preferably N(Ar), C(R b ) 2 , O or S, wherein R b has the definition detailed in Claim 1 ; Y 1 , Y 2 are in each case identical or different and are N(Ar), N(R), P(Ar), P(R), P(=O)Ar, P(=O) R, P(=S)Ar, P(=S)R, B(Ar), B(R), Al(Ar), Al(R), Ga(Ar), Ga(R), C=O, C(R) 2 , Si(R) 2 , Ge(R) 2 , C=NR, C=NAr, C=C(R) 2 , C=C(R)(Ar), O, S, Se, S=O or SO 2 , preferably N(Ar), N(R), B(Ar), B(R), P(=O)R, P(=O)Ar, C=O, C( R) 2 , C=C(R) 2 , C=C(R)(Ar), Si(R) 2 , O, S, Se, S=O or SO 2 , more preferably N(Ar), C (R) 2 , O or S, wherein R has the definition specified in Claim 1; X is in each case the same or different and is N or CR, the prerequisite being an X group in one ring not more than two are N, where R has the definition specified in claim 1; X a is in each case the same or different and is N or CR a , with the prerequisite that the group X a is in a ring No more than two groups are N, where R a has the definition specified in claim 1; X b is in each case the same or different and is N or CR b , the prerequisite being X in one ring No more than two groups of b are N, wherein R b has the definition specified in Claim 1. 根據請求項1或2之化合物，其包括至少一個式(III-1)至(III-41)之結構：
Figure 03_image089
Figure 03_image091
Figure 03_image093
Figure 03_image095
Figure 03_image097
Figure 03_image099
Figure 03_image101
Figure 03_image103
Figure 03_image105
Figure 03_image107
Figure 03_image109
Figure 03_image111
Figure 03_image113
Figure 03_image115
Figure 03_image117
Figure 03_image119
Figure 03_image121
Figure 03_image123
Figure 03_image125
Figure 03_image127
Figure 03_image129
Figure 03_image131
Figure 03_image133
Figure 03_image135
Figure 03_image137
Figure 03_image139
Figure 03_image141
Figure 03_image143
Figure 03_image145
Figure 03_image147
Figure 03_image149
Figure 03_image151
Figure 03_image153
Figure 03_image155
Figure 03_image157
Figure 03_image159
Figure 03_image161
Figure 03_image163
Figure 03_image165
Figure 03_image167
Figure 03_image169
其中符號Y 1、Y 2、Y a、Y b、X、X a和X b具有以請求項2給出之定義。 According to the compound of claim 1 or 2, it comprises at least one structure of formula (III-1) to (III-41):
Figure 03_image089
Figure 03_image091
Figure 03_image093
Figure 03_image095
Figure 03_image097
Figure 03_image099
Figure 03_image101
Figure 03_image103
Figure 03_image105
Figure 03_image107
Figure 03_image109
Figure 03_image111
Figure 03_image113
Figure 03_image115
Figure 03_image117
Figure 03_image119
Figure 03_image121
Figure 03_image123
Figure 03_image125
Figure 03_image127
Figure 03_image129
Figure 03_image131
Figure 03_image133
Figure 03_image135
Figure 03_image137
Figure 03_image139
Figure 03_image141
Figure 03_image143
Figure 03_image145
Figure 03_image147
Figure 03_image149
Figure 03_image151
Figure 03_image153
Figure 03_image155
Figure 03_image157
Figure 03_image159
Figure 03_image161
Figure 03_image163
Figure 03_image165
Figure 03_image167
Figure 03_image169
Wherein the symbols Y 1 , Y 2 , Y a , Y b , X, X a and X b have the definitions given in Claim 2. 根據請求項1至3中一或多項之化合物，其包括至少一個式(IV-1)至(IV-41)之結構：
Figure 03_image171
Figure 03_image173
Figure 03_image175
Figure 03_image177
Figure 03_image179
Figure 03_image181
Figure 03_image183
Figure 03_image185
Figure 03_image187
Figure 03_image189
Figure 03_image191
Figure 03_image193
Figure 03_image195
Figure 03_image197
Figure 03_image199
Figure 03_image201
Figure 03_image203
Figure 03_image205
Figure 03_image207
Figure 03_image209
Figure 03_image211
Figure 03_image213
Figure 03_image215
Figure 03_image217
Figure 03_image219
Figure 03_image221
Figure 03_image223
Figure 03_image225
Figure 03_image227
Figure 03_image229
Figure 03_image231
Figure 03_image233
Figure 03_image235
Figure 03_image237
Figure 03_image239
Figure 03_image241
Figure 03_image243
Figure 03_image245
Figure 03_image247
Figure 03_image249
Figure 03_image251
其中符號R、R a和R b具有以請求項1給出之定義，符號Y 1、Y 2、Y a和Y b具有以請求項2給出之定義，且其他符號具有以下定義： m    為0、1、2、3或4； j     為0、1或2。 Compounds according to one or more of claims 1 to 3, comprising at least one structure of formulas (IV-1) to (IV-41):
Figure 03_image171
Figure 03_image173
Figure 03_image175
Figure 03_image177
Figure 03_image179
Figure 03_image181
Figure 03_image183
Figure 03_image185
Figure 03_image187
Figure 03_image189
Figure 03_image191
Figure 03_image193
Figure 03_image195
Figure 03_image197
Figure 03_image199
Figure 03_image201
Figure 03_image203
Figure 03_image205
Figure 03_image207
Figure 03_image209
Figure 03_image211
Figure 03_image213
Figure 03_image215
Figure 03_image217
Figure 03_image219
Figure 03_image221
Figure 03_image223
Figure 03_image225
Figure 03_image227
Figure 03_image229
Figure 03_image231
Figure 03_image233
Figure 03_image235
Figure 03_image237
Figure 03_image239
Figure 03_image241
Figure 03_image243
Figure 03_image245
Figure 03_image247
Figure 03_image249
Figure 03_image251
wherein the symbols R, R a and R b have the definitions given in claim 1, the symbols Y 1 , Y 2 , Y a and Y b have the definitions given in claim 2, and the other symbols have the following definitions: m is 0, 1, 2, 3 or 4; j is 0, 1 or 2. 根據請求項1至4中一或多項之化合物，其包括至少一個式(V-1)至(V-8)之結構：
Figure 03_image253
Figure 03_image255
Figure 03_image257
其中符號R a和R b具有以請求項1給出之定義且其他符號具有以下定義： R c、R d在各情況下為相同的或不同的且為N(Ar') 2、N(R 1) 2、C(=O)N(Ar') 2、C(=O)N(R 1) 2、C(Ar') 3、C(R 1) 3、Si(Ar') 3、Si(R 1) 3、B(Ar') 2、B(R 1) 2、C(=O)Ar'、C(=O)R 1、P(=O)(Ar') 2、P(=O)(R 1) 2、P(Ar') 2、P(R 1) 2、S(=O)Ar'、S(=O)R 1、S(=O) 2Ar'、S(=O) 2R 1、OSO 2Ar'、OSO 2R 1、具有1至40個碳原子的直鏈烷基、烷氧基或硫烷氧基、或具有2至40個碳原子的烯基或炔基、或具有3至20個碳原子的支鏈或環狀烷基、烷氧基或硫烷氧基，其中該等烷基、烷氧基、硫烷氧基、烯基或炔基可在各例子中經一或多個R 1基團取代，其中一或多個不相鄰的CH 2基團可經R 1C=CR 1、C≡C、Si(R 1) 2、C=O、C=S、C=Se、C=NR 1、-C(=O)O-、-C(=O)NR 1-、NR 1、P(=O)(R 1)、 -O-、-S-、SO或SO 2置換、或具有5至60個芳族環原子且可在各例子中經一或多個R 1基團取代之芳族或雜芳族環系統、或具有5至60個芳族環原子且可經一或多個R 1基團取代之芳氧基或雜芳氧基；或具有5至60個芳族環原子且可經一或多個R 1基團取代之雜芳硫基、或具有5至60個芳族環原子且可經一或多個R 1基團取代之二芳胺基、芳基雜芳胺基、二雜芳胺基、或具有5至60個芳族環原子及在烷基中的1至10個碳原子且可經一或多個R 1基團取代之芳基烷基或雜芳基烷基；同時，一個R c基團可與R、R a、R b、R d基團或另一基團形成環系統；同時，R d基團可與R、R a、R b、R c基團或另一基團形成環系統； m    為0、1、2、3或4； n    為0、1、2或3。 Compounds according to one or more of claims 1 to 4, comprising at least one structure of formulas (V-1) to (V-8):
Figure 03_image253
Figure 03_image255
Figure 03_image257
where the symbols R a and R b have the definitions given in claim 1 and the other symbols have the following definitions: R c , R d are in each case the same or different and are N(Ar') 2 , N(R 1 ) 2 , C(=O)N(Ar') 2 , C(=O)N(R 1 ) 2 , C(Ar') 3 , C(R 1 ) 3 , Si(Ar') 3 , Si (R 1 ) 3 , B(Ar') 2 , B(R 1 ) 2 , C(=O)Ar', C(=O)R 1 , P(=O)(Ar') 2 , P(= O)(R 1 ) 2 , P(Ar') 2 , P(R 1 ) 2 , S(=O)Ar', S(=O)R 1 , S(=O) 2 Ar', S(= O) 2 R 1 , OSO 2 Ar', OSO 2 R 1 , straight-chain alkyl, alkoxy or thioalkoxy having 1 to 40 carbon atoms, or alkenyl having 2 to 40 carbon atoms or Alkynyl, or branched or cyclic alkyl, alkoxy or thioalkoxy having 3 to 20 carbon atoms, wherein such alkyl, alkoxy, thioalkoxy, alkenyl or alkynyl can be Substituted in each case by one or more R 1 groups, wherein one or more non-adjacent CH 2 groups can be substituted by R 1 C=CR 1 , C≡C, Si(R 1 ) 2 , C= O, C=S, C=Se, C=NR 1 , -C(=O)O-, -C(=O)NR 1 -, NR 1 , P(=O)(R 1 ), -O- , -S-, SO or SO substituted , or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms and which may in each case be substituted by one or more R groups, or having 5 Aryloxy or heteroaryloxy groups having up to 60 aromatic ring atoms and which may be substituted by one or more R groups; or having 5 to 60 aromatic ring atoms and which may be substituted by one or more R groups A substituted heteroarylthio group, or a diarylamine group having 5 to 60 aromatic ring atoms which may be substituted by one or more R groups, an arylheteroarylamine group, a diheteroarylamino group, or a Arylalkyl or heteroarylalkyl groups of 5 to 60 aromatic ring atoms and 1 to 10 carbon atoms in the alkyl group which may be substituted by one or more R groups; at the same time, one R group group can form a ring system with R, Ra , Rb , Rd group or another group; at the same time, Rd group can form a ring system with R, Ra, Rb , Rc group or another group Ring system; m is 0, 1, 2, 3 or 4; n is 0, 1, 2 or 3. 根據請求項1至5中一或多項之化合物，其中至少一個R、R a、R b、R c、R d基團為具有1至40個碳原子的直鏈烷基、烷氧基或硫烷氧基、或具有2至40個碳原子的烯基或炔基、或具有3至20個碳原子的支鏈或環狀烷基、烷氧基或硫烷氧基，其中該等烷基、烷氧基、硫烷氧基、烯基或炔基可在各例子中經一或多個R 1基團取代，其中一或多個不相鄰的CH 2基團可經R 1C=CR 1、C≡C、Si(R 1) 2、C=O、C=S、C=Se、C=NR 1、-C(=O)O-、 -C(=O)NR 1-、NR 1、P(=O)(R 1)、-O-、-S-、SO或SO 2置換、或具有5至60個芳族環原子且可在各例子中經一或多個R 1基團取代之芳族或雜芳族環系統。 Compounds according to one or more of claims 1 to 5, wherein at least one R, R a , R b , R c , R d group is a linear alkyl, alkoxy or sulfur group having 1 to 40 carbon atoms Alkoxy, or alkenyl or alkynyl having 2 to 40 carbon atoms, or branched or cyclic alkyl, alkoxy or thioalkoxy having 3 to 20 carbon atoms, wherein the alkyl , alkoxy, thioalkoxy, alkenyl or alkynyl may in each case be substituted by one or more R 1 groups, wherein one or more non-adjacent CH 2 groups may be substituted by R 1 C= CR 1 , C≡C, Si(R 1 ) 2 , C=O, C=S, C=Se, C=NR 1 , -C(=O)O-, -C(=O)NR 1 -, NR 1 , P(=O)(R 1 ), -O-, -S-, SO or SO 2 substituted, or having 5 to 60 aromatic ring atoms and in each case via one or more R 1 Aromatic or heteroaromatic ring systems substituted by radicals. 根據請求項1至6中一或多項之化合物，其中至少兩個R、R a、R b、R c、R d基團與該兩個R、R a、R b、R c、R d基團結合之其他基團一起形成稠合環，其中該兩個R、R a、R b、R c、R d基團形成至少一個式(RA-1)至(RA-12)之結構：
Figure 03_image259
Figure 03_image261
其中R 1具有上文詳述之定義，虛線鍵表示該兩個R、R a、R b、R c、R d基團經由其結合至其他基團之連接位點，且其他符號具有以下定義： Y 3在各情況下為相同的或不同的且為C(R 1) 2、 (R 1) 2C-C(R 1) 2、(R 1)C=C(R 1)、NR 1、NAr'、O或S； R e在各情況下為相同的或不同的且為F、具有1至40個碳原子的直鏈烷基、烷氧基或硫烷氧基、或具有2至40個碳原子的烯基或炔基、或具有3至20個碳原子的支鏈或環狀烷基、烷氧基或硫烷氧基，其中該等烷基、烷氧基、硫烷氧基、烯基或炔基可在各例子中經一或多個R 2基團取代，其中一或多個不相鄰的CH 2基團可經R 2C=CR 2、C≡C、Si(R 2) 2、C=O、C=S、C=Se、C=NR 2、-C(=O)O-、-C(=O)NR 2-、NR 2、P(=O)(R 1)、 -O-、-S-、SO或SO 2置換、或具有5至60個芳族環原子且可在各例子中經一或多個R 2基團取代之芳族或雜芳族環系統、或具有5至60個芳族環原子且可經一或多個R 2基團取代之芳氧基或雜芳氧基；同時，兩個R e基團一起或一個R e基團與R 1基團或與另一基團一起形成環系統； s     為0、1、2、3、4、5或6； t     為0、1、2、3、4、5、6、7或8； v    為0、1、2、3、4、5、6、7、8或9。 Compounds according to one or more of claims 1 to 6, wherein at least two R, R a , R b , R c , R d groups and the two R, R a , R b , R c , R d groups The other groups combined together form a fused ring, wherein the two R, R a , R b , R c , R d groups form at least one structure of formulas (RA-1) to (RA-12):
Figure 03_image259
Figure 03_image261
wherein R 1 has the definition detailed above, the dotted bond indicates the linking site through which the two R, R a , R b , R c , R d groups are bound to other groups, and the other symbols have the following definitions : Y 3 is the same or different in each case and is C(R 1 ) 2 , (R 1 ) 2 CC(R 1 ) 2 , (R 1 )C=C(R 1 ), NR 1 , NAr ', O or S; R is in each case the same or different and is F, a linear alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms, or having 2 to 40 Alkenyl or alkynyl of carbon atoms, or branched or cyclic alkyl, alkoxy or thioalkoxy having 3 to 20 carbon atoms, wherein such alkyl, alkoxy, thioalkoxy, Alkenyl or alkynyl groups may in each case be substituted by one or more R2 groups, wherein one or more non-adjacent CH2 groups may be substituted by R2C = CR2 , C≡C, Si(R 2 ) 2 , C=O, C=S, C=Se, C=NR 2 , -C(=O)O-, -C(=O)NR 2 -, NR 2 , P(=O)(R 1 ), -O-, -S-, SO or SO substituted , or aromatic or heteroaromatic having 5 to 60 aromatic ring atoms and which may in each case be substituted by one or more R groups ring system, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms which may be substituted by one or more R groups ; at the same time, two R groups together or one R group form a ring system with the R group or with another group; s is 0, 1, 2, 3, 4, 5 or 6; t is 0, 1, 2, 3, 4, 5, 6, 7 or 8; v is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9. 根據請求項1至7中一或多項之化合物，其中至少兩個R、R a、R b、R c、R d基團與該兩個R、R a、R b、R c、R d基團結合之其他基團一起形成稠合環，其中該兩個R、R a、R b、R c、R d基團形成式(RB)之結構：
Figure 03_image263
其中R 1具有以請求項1詳述之定義，虛線鍵表示該兩個R、R a、R b、R c、R d基團經由其結合至其他基團之連接位點，標號m為0、1、2、3或4，且Y 4為C(R 1) 2、NR 1、NAr'、BR 1、BAr'、O或S。 Compounds according to one or more of claims 1 to 7, wherein at least two R, R a , R b , R c , R d groups and the two R, R a , R b , R c , R d groups The other groups bound together form a fused ring, wherein the two R, R a , R b , R c , R d groups form a structure of formula (RB):
Figure 03_image263
Wherein R 1 has the definition detailed in Claim 1, the dotted line bond represents the linking site through which the two R, R a , R b , R c , R d groups are bound to other groups, and the label m is 0 , 1, 2, 3 or 4, and Y 4 is C(R 1 ) 2 , NR 1 , NAr′, BR 1 , BAr′, O or S. 根據請求項1至8中一或多項之化合物，其包含至少一個式(VI-1)至(VI-22)之結構，其中該化合物具有至少一個稠合環，
Figure 03_image265
Figure 03_image267
Figure 03_image269
Figure 03_image271
Figure 03_image273
Figure 03_image275
Figure 03_image277
其中符號R、R a、R b、Y 1和Y 2具有以請求項1或請求項2給出之定義，符號o表示連接位點，且其他符號具有以下定義： m    為0、1、2、3或4； n    為0、1、2或3； j     為0、1或2。 A compound according to one or more of claims 1 to 8, comprising at least one structure of formulas (VI-1) to (VI-22), wherein the compound has at least one fused ring,
Figure 03_image265
Figure 03_image267
Figure 03_image269
Figure 03_image271
Figure 03_image273
Figure 03_image275
Figure 03_image277
Wherein the symbols R, R a , R b , Y 1 and Y 2 have the definitions given in claim item 1 or claim item 2, the symbol o represents the linking site, and other symbols have the following definitions: m is 0, 1, 2 , 3 or 4; n is 0, 1, 2 or 3; j is 0, 1 or 2. 根據請求項1至9中一或多項之化合物，其中至少一個取代基R、R a、R b在各情況下為相同的或不同的且選自由下列所組成之群組：H、D、具有3至20個碳原子的支鏈或環狀烷基、烷氧基或硫烷氧基、或選自下式Ar-1至Ar-78之群組的芳族或雜芳族環系統：
Figure 03_image279
Figure 03_image281
Figure 03_image283
Figure 03_image285
Figure 03_image287
Figure 03_image289
Figure 03_image291
Figure 03_image293
Figure 03_image295
Figure 03_image297
Figure 03_image299
Figure 03_image301
其中R 1具有上文給出之定義，虛線鍵表示在對應基團上的鍵，且另外： Ar 1在各情況下為相同的或不同的且為具有6至18個芳族環原子且可在各例子中經一或多個R 1基團取代之二價芳族或雜芳族環系統； A    在各情況下為相同的或不同的且為C(R 1) 2、NR 1、O或S； p    為0或1，其中p = 0意指Ar 1基團不存在且對應的芳族或雜芳族基團係直接鍵結至對應基團； q    為0或1，其中q=0意指沒有A基團在此位置上鍵結，且R 1基團反而鍵結至對應的碳原子。 Compounds according to one or more of claims 1 to 9, wherein at least one substituent R, Ra , Rb is in each case the same or different and is selected from the group consisting of H, D, having Branched or cyclic alkyl, alkoxy or thioalkoxy groups of 3 to 20 carbon atoms, or aromatic or heteroaromatic ring systems selected from the group of the following formulas Ar-1 to Ar-78:
Figure 03_image279
Figure 03_image281
Figure 03_image283
Figure 03_image285
Figure 03_image287
Figure 03_image289
Figure 03_image291
Figure 03_image293
Figure 03_image295
Figure 03_image297
Figure 03_image299
Figure 03_image301
wherein R has the definition given above, the dotted bond represents the bond on the corresponding group, and in addition: Ar are in each case the same or different and have 6 to 18 aromatic ring atoms and can A divalent aromatic or heteroaromatic ring system substituted in each case by one or more R 1 groups; A is in each case the same or different and is C(R 1 ) 2 , NR 1 , O or S; p is 0 or 1, where p = 0 means that the Ar group does not exist and the corresponding aromatic or heteroaromatic group is directly bonded to the corresponding group; q is 0 or 1 , where q= 0 means that no A group is bonded at this position, and the R group is instead bonded to the corresponding carbon atom. 根據前述請求項5至10中至少一項之化合物，其中該取代基R c、R d在各情況下為相同的或不同的且表示具有6至30個芳族環原子且可經一或多個R 1基團取代之芳族或雜芳族環系統，其係選自請求項10中所示之式(Ar-1)至(Ar-78)之群組。 A compound according to at least one of the preceding claims 5 to 10, wherein the substituents R c , R d are in each case the same or different and represent 6 to 30 aromatic ring atoms and can be modified by one or more An aromatic or heteroaromatic ring system substituted by R 1 groups selected from the group of formulas (Ar-1) to (Ar-78) shown in claim 10. 根據前述請求項1至11中至少一項之化合物，其中該化合物包括僅兩個或僅三個式(I)、(II-1)至(II-42)、(III-1)至(III-41)、(IV-1)至(IV-41)、(V-1)至(V-8)及/或(VI-1)至(VI-22)之結構。The compound according to at least one of the preceding claims 1 to 11, wherein the compound comprises only two or only three formulas (I), (II-1) to (II-42), (III-1) to (III -41), (IV-1) to (IV-41), (V-1) to (V-8) and/or (VI-1) to (VI-22) structures. 一種寡聚物、聚合物或樹枝狀聚合物，其含有一或多種根據請求項1至11中任一項之化合物，其中不以氫原子或取代基而以該化合物的一或多個鍵連接至該聚合物、寡聚物或樹枝狀聚合物。A kind of oligomer, polymkeric substance or dendritic polymer, it contains one or more compounds according to any one of claim item 1 to 11, wherein not with hydrogen atom or substituting group but with one or more bonds of this compound link to the polymer, oligomer or dendrimer. 一種調配物，其包含至少一種根據請求項1至12中一或多項之化合物、或根據請求項13之寡聚物、聚合物或樹枝狀聚合物及至少一種其他化合物，其中該其他化合物較佳地選自一或多種溶劑。A formulation comprising at least one compound according to one or more of claims 1 to 12, or an oligomer, polymer or dendrimer according to claim 13 and at least one other compound, wherein the other compound is preferably selected from one or more solvents. 一種組成物，其包含至少一種式(I)化合物
Figure 03_image303
其中所使用之符號具有以請求項1給出之定義、或如請求項13之寡聚物、聚合物或樹枝狀聚合物及至少一種選自由下列所組成之群組的其他化合物：螢光發光體、磷光發光體、展現TADF之發光體、主體材料、電子傳輸材料、電子注入材料、電洞傳導材料、電洞注入材料、電子阻擋材料和電洞阻擋材料。 A composition comprising at least one compound of formula (I)
Figure 03_image303
The symbols used therein have the definitions given in Claim 1, or oligomers, polymers or dendrimers as in Claim 13 and at least one other compound selected from the group consisting of: Fluorescence Phosphorescent emitters, emitters exhibiting TADF, host materials, electron transport materials, electron injection materials, hole conduction materials, hole injection materials, electron blocking materials, and hole blocking materials. 一種製備根據請求項1至12中一或多項之化合物之方法，其特徵在於合成具有W a基團中至少一者或W a基團中一者之前驅物的基礎骨架且藉助於親核性芳族取代反應或偶合反應引入芳族或雜芳族基團。 A process for the preparation of compounds according to one or more of claims 1 to 12, characterized in that a basic skeleton with at least one of the W a groups or a precursor of one of the W a groups is synthesized and by means of nucleophilic Aromatic substitution or coupling reactions introduce aromatic or heteroaromatic groups. 一種式(I)化合物
Figure 03_image305
其中所使用之符號具有以請求項1給出之定義、或根據請求項13之寡聚物、聚合物或樹枝狀聚合物在電子裝置中之用途。 A compound of formula (I)
Figure 03_image305
The symbols used therein have the definitions given in claim 1, or the use of oligomers, polymers or dendrimers according to claim 13 in electronic devices. 一種電子裝置，其包含至少一種式(I)化合物
Figure 03_image307
其中所使用之符號具有以請求項1給出之定義、或根據請求項13之寡聚物、聚合物或樹枝狀聚合物。 An electronic device comprising at least one compound of formula (I)
Figure 03_image307
The symbols used therein have the definitions given in claim 1, or oligomers, polymers or dendrimers according to claim 13.
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